Month: October 2022

Denk, Michael K’s team published research in Chemosphere in 2019-10-31 | 606-68-8

Chemosphere published new progress about C-H bond energy. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Electric Literature of 606-68-8.

Denk, Michael K.; Milutinovic, Nicholas S.; Dereviankin, Mikhail Y. published the artcile< Reduction of halocarbons to hydrocarbons by NADH models and NADH>, Electric Literature of 606-68-8, the main research area is halocarbon reduction bond dissociation energy toxicol; Bond dissociation energy; DDT; Halocarbons; Metabolic disruption; NADH; Toxicology.

The reduction of halocarbons by NADH models and NADH under ambient conditions is reported as a new type of reactivity pointing towards a hitherto unknown disruptive pathway for NADH/NADPH-dependent processes. The reaction was studied with the omnipresent pesticide DDT, the inhalation anesthetic halothane, and several simple halocarbons. The halide-hydride exchange represents a biochem. equivalent for the reduction of halocarbons by traditional synthetic reagents like silanes (R3Si-H) and stannanes (R3Sn-H). High precision thermochem. calculations (CBS-QB3) reveal the carbon-hydrogen bond dissociation energy of NADH (70.8 kcal·mol-1) to be lower than that of stannane (SnH4: 78.1 kcal·mol-1), approaching that of the elusive plumbane (PbH4: 68.9 kcal·mol-1). The ready synthetic accessibility of NADH models, their low carbon-hydrogen bond dissociation energy, and their dehalogenation activity in the presence of air and moisture recommend these compounds as substitutes for the air-sensitive or toxic metal hydrides currently employed in synthesis.

Chemosphere published new progress about C-H bond energy. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Electric Literature of 606-68-8.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Tanielyan, Setrak K’s team published research in Organic Process Research & Development in 2006-10-31 | 325168-88-5

Organic Process Research & Development published new progress about 325168-88-5. 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, HPLC of Formula: 325168-88-5.

Tanielyan, Setrak K.; Marin, Norman; Alvez, Gabriela; Augustine, Robert L. published the artcile< Two Efficient Enantioselective Syntheses of 2-Amino-1-phenylethanol>, HPLC of Formula: 325168-88-5, the main research area is aminophenylethanolstereoselective preparation.

Two enantioselective methods for the synthesis of 2-amino-1-phenylethanol have been developed. The first uses an enantioselective oxazaborolidine-catalyzed borane reduction of 2-chloroacetophenone (phenacyl chloride) to give the chiral chloro alc. in good yield with an ee in the 93-97% range. Reaction with dilute ammonium hydroxide produced the amino alc. in good yield with a high ee. The second approach involved the conversion of phenacyl chloride to the succinimidoacetophenone which was then hydrogenated using a chiral ruthenium complex in conjunction with a base and an optically active amine (Noyori procedure). This gave the optically active succinimido alc. in very good yield with an ee of 98%. Hydrolysis with dilute base produced the optically active amino alc. in very good yield and excellent enantioselectivity.

Organic Process Research & Development published new progress about 325168-88-5. 325168-88-5 belongs to class chiral-phosphine-ligands, and the molecular formula is C48H50P2, HPLC of Formula: 325168-88-5.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Luo, Mingfang’s team published research in Chinese Science Bulletin in 2003-02-28 | 606-68-8

Chinese Science Bulletin published new progress about Acidovorax delafieldii. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Application of C21H27N7Na2O14P2.

Luo, Mingfang; Xing, Jianmin; Gou, Zhongxuan; Li, Shan; Xie, Yuchun; Liu, Huizhou; Chen, Jiayong published the artcile< Effects of aqueous media on microbial removal of sulfur from dibenzothiophene in the presence of hydrocarbons>, Application of C21H27N7Na2O14P2, the main research area is dibenzothiophene microbial desulfurization bacteria hydrocarbon; biodesulfurization dibenzothiophene bacteria hydrocarbon.

Effects of the aqueous components, pH, concentration of NaCl, and volume ratios of oil-to-water on the desulfurization activity of gram-neg. desulfurizing bacterium, Pseudomonas delafieldii R-8, were investigated. R-8 showed high desulfurization activity even with a concentration of NaCl up to 60 g · L-1 or high content of dodecane over 83%. The addition of NADH could increase the desulfurization activity. The desulfurization of DBT could be proceeded in the presence of hydrocarbons with the carbon length ranging from 6 to 16. Among them, the highest specific desulfurization activity was shown in dodecane, the value of which was 1.96 mg · g-1 · h-1 similar to that of R. erythropolis IGTS8.

Chinese Science Bulletin published new progress about Acidovorax delafieldii. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Application of C21H27N7Na2O14P2.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Yoshizaki, Soichi’s team published research in Organic Letters in 2016-02-05 | 139139-93-8

Organic Letters published new progress about [2+2+2] Cycloaddition reaction. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Reference of 139139-93-8.

Yoshizaki, Soichi; Nakamura, Yu; Masutomi, Koji; Yoshida, Tomoka; Noguchi, Keiichi; Shibata, Yu; Tanaka, Ken published the artcile< Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of 1,6-Enynes with Cyclopropylideneacetamides>, Reference of 139139-93-8, the main research area is asym cycloaddition enyne cyclopropylideneacetamide rhodium catalyst.

It has been established that a cationic rhodium(I)/(S)-H8-BINAP complex catalyzes the asym. [2+2+2] cycloaddition of 1,6-enynes with cyclopropylideneacetamides to produce spirocyclohexenes in excellent enantioselectivity with retaining cyclopropane rings. E.g., in presence of [Rh(cod)2]BF4 and (S)-H8-BINAP, [2+2+2] cycloaddition of MeCCCH2NTsCH2CMe:CH2 and N-methyl-N-phenylcyclopropylideneacetamide gave 69% I (>99%ee).

Organic Letters published new progress about [2+2+2] Cycloaddition reaction. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Reference of 139139-93-8.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Lautens, Mark’s team published research in Organic Letters in 2000-06-15 | 277306-29-3

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, SDS of cas: 277306-29-3.

Lautens, Mark; Fagnou, Keith; Taylor, Mark published the artcile< Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with phenols>, SDS of cas: 277306-29-3, the main research area is oxabicyclic alkene asym ring opening phenol; rhodium asym ring opening oxabicyclic alkene; stereoselective enantioselective aryloxydihydronaphthalenol preparation.

The scope of the rhodium-catalyzed asym. ring opening reaction of oxabenzonorbornadiene has been extended to include phenolic nucleophiles XC6H4OH (X = 4-F, 4-Cl, 4-Br, 4-I, 4-MeCO, 4-F3C, 4-Me, 4-NC, 2-Br, 3-Br). The enantioenriched, functionalized dihydronaphthalene products, e.g., aryloxydihydronaphthalenol I, are highly valuable intermediates for which no other practical methods of preparation are available. Using [Rh(CO)2Cl]2 as the rhodium source and ferrocene II as the diphosphine ligand allows the use of less reactive o-halophenols in the stereoselective ring opening reaction. The utility of these products has been demonstrated through their application in the synthesis of benzofuran polycyclic materials, e.g, III.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, SDS of cas: 277306-29-3.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Fialho, David M.’s team published research in Organic Letters in 2021 | CAS: 256390-47-3

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]

Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]On May 7, 2021 ,《Copper-Catalyzed Asymmetric Reductions of Aryl/Heteroaryl Ketones under Mild Aqueous Micellar Conditions》 appeared in Organic Letters. The author of the article were Fialho, David M.; Etemadi-Davan, Elham; Langner, Olivia C.; Takale, Balaram S.; Gadakh, Amol; Sambasivam, Ganesh; Lipshutz, Bruce H.. The article conveys some information:

Enantioselective syntheses of nonracemic secondary alcs. have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2.H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodol. serves as a green protocol to access enantio-enriched alcs. under mild conditions (0-22°C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alc. products are formed in good to excellent yields with ee values greater than 90%. In the experiment, the researchers used (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine])

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine](cas: 256390-47-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Quality Control of (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine]

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Zheng, Long-Sheng’s team published research in Organic Letters in 2020 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

《Asymmetric Hydrogenation of 2-Aryl-3-phthalimidopyridinium Salts: Synthesis of Piperidine Derivatives with Two Contiguous Stereocenters》 was published in Organic Letters in 2020. These research results belong to Zheng, Long-Sheng; Wang, Fangyuan; Ye, Xiang-Yu; Chen, Gen-Qiang; Zhang, Xumu. Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole The article mentions the following:

Asym. hydrogenation of 2-aryl-3-phthalimidopyridinium salts catalyzed by the Ir/SegPhos catalytic system was described, leading to the corresponding chiral piperidine derivatives bearing two contiguous chiral centers, with high levels of enantioselectivities and diastereoselectivities. A gram-scale experiment has demonstrated the utility of this approach. The phthaloyl group could be easily removed and then smoothly converted to key intermediate (+)-CP-99994 as one of the neurokinin 1 receptor antagonists.(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole) was used in this study.

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives or diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex.Quality Control of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Mifleur, Alexis’s team published research in Catalysis Letters in 2021 | CAS: 210169-54-3

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Recommanded Product: 210169-54-3

Mifleur, Alexis; Suisse, Isabelle; Mortreux, Andre; Sauthier, Mathieu published their research in Catalysis Letters in 2021. The article was titled 《Enantioselective Nickel Catalyzed Butadiene Hydroalkoxylation with Ethanol: from Experimental Results to Kinetics Parameters》.Recommanded Product: 210169-54-3 The article contains the following contents:

The enantioselective hydroalkoxylation of butadiene with ethanol has been performed in the presence of nickel-based catalysts and chiral diphosphine ligands. Ee’s up to 77% could be obtained from the use of atropoisomeric chiral ligands such as Segphos. The kinetics parameters of the reaction were determined using a qual. kinetic model to better explain the l/b isomerization and racemization processes observed for long reaction times. The experimental part of the paper was very detailed, including the reaction process of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Recommanded Product: 210169-54-3)

(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans.Recommanded Product: 210169-54-3

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Germain, Nicolas’s team published research in Organic Letters in 2014 | CAS: 1156547-61-3

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

《Domino Asymmetric Conjugate Addition-Conjugate Addition》 was written by Germain, Nicolas; Schlaefli, Doriane; Chellat, Mathieu; Rosset, Stephane; Alexakis, Alexandre. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene And the article was included in Organic Letters on April 4 ,2014. The article conveys some information:

In the presence of copper catalysts and nonracemic phosphoramidite, imidazolium, or aminoferrocenylphosphine ligands, ethylmagnesium bromide, trimethylaluminum, and dimethyl- and diethylzinc underwent enantioselective and diastereoselective conjugate addition reactions to cyclopentenones, cyclohexenones, and cycloheptenones followed by trapping with either nitroalkenes or 1,1-bis(phenylsulfonyl)ethylene to give oxoalkyl cycloalkanones in 63-85% yields, 57:43-97:3 dr, and in 86->99.5% ee; the oxoalkyl cycloalkanones were converted by various methods to indenones, a hydrazulenone, a tetrahydrobenzofuran and a tetrahydroindole, and an octahydronaphthalene. In the experiment, the researchers used many compounds, for example, (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene)

(1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene(cas: 1156547-61-3) belongs to chiral phosphine ligands. Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates. These intermediates are formed through nucleophilic attack of the phosphine catalysts at electron-poor nuclei (normally carbon atoms) and then proceed through several steps to form new chemical bonds. Application In Synthesis of (1S)-1-(Dicyclohexylphosphino)-2-[(R)-[2-(dicyclohexylphosphino)phenyl](dimethylamino)methyl]ferrocene

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Kawamura, Kenjiro’s team published research in Organic Letters in 2008 | CAS: 286454-86-2

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

《Novel N,N,P-Tridentate Ligands for the Highly Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones》 was written by Kawamura, Kenjiro; Fukuzawa, Hitomi; Hayashi, Masahiko. Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine And the article was included in Organic Letters on August 21 ,2008. The article conveys some information:

Use of 0.25 mol % of the N,N,P-tridentate ligands (S)-QuCH:NCHRCH2PPh2 (Qu = 2-quinolyl) and 0.1 mol % of Cu(OTf)2 enabled the enantioselective 1,4-addition of dialkylzincs to cyclic enones to produce 1,4-adducts in up to 99% ee.(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine) was used in this study.

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Safety of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis