Category: 17261-28-8

17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of acetato complex 3 (26.7 mg, 0.04 mmol) in CH2Cl2 (5 mL), a solution of 2-(diphenylphosphino)benzoic acid (24.6 mg, 0.08 mmol) in CH2Cl2 (5 mL) was added. The reaction mixture was stirred at ambient temperature for 5 h. The resulting solution was concentrated to half of the initial volume, and n-hexane(20 mL) was added. The precipitate was collected and dried in vacuo affording the product as a white powder (14.7 mg, 0.03 mmol, 75percent). 1H NMR (600 MHz, CDCl3):d 9.14 (s, 1 H, Hh), 8.30?8.28 (m, 1 H, Dpb?H), 7.71 (t, 1H, Hf, 3JH,H = 6 Hz), 7.48?7.26 (m, 12 H, He, Hg, Dpb?H), 6.95 (d, 1 H, Hd, 3JH,H = 6 Hz), 6.85?6.80 (m, 2 H, Ha,Dpb?H), 6.72 (t, 1 H, Hc, 3JH,H = 6 Hz), 6.36 (t, 1 H, Hb,3JH,H = 6 Hz), 4.28 (br s, 2 H, CH2). 13C NMR (150 MHz,CDCl3): d 170.5 (d, CO, 3JC,P = 4.2 Hz), 158.7 (Ck), 151.3(Ch), 148.2 (d, Cj, 2JC,P = 1.5 Hz), 143.7 (d, Dpb?C,JC,P = 13 Hz), 140.9 (d, Ca, 3JC,P = 12 Hz), 139.4 (Cf),138.8 (Ci), 135.3 (d, Dpb?C, JC,P = 13 Hz), 133.8 (d,Dpb?C, JC,P = 9 Hz), 132.1 (d, Dpb?C, JC,P = 4.5 Hz),131.4 (d, Dpb?C, JC,P = 1.5 Hz), 130.1 (d, Dpb?C,JC,P = 9 Hz), 129.2, 128.5, 128.2 (Dpb?C), 127.1 (Cd),126.0 (d, Cb, 4JC,P = 4.5 Hz), 124.3 (Cc), 124.1 (d, Ce,4JC,P = 3 Hz), 123.0 (d, Cg, 4JC,P = 3 Hz), 49.9 (CH2).31P NMR (100 MHz, CDCl3): d 33.2 (s, PDbp). ESI?MS(positive) m/z: 580 [M ? H]?. mmax/cm-1 (KBr): 1609(CO). Anal. Calcd. for C31H25NO2PPd: C, 64.20; H, 4.17;N, 2.42percent; Found: C, 64.11; H, 4.546; N, 2.14percent., 17261-28-8

17261-28-8 2-(Diphenylphosphino)benzoic acid 87021, achiral-phosphine-ligands compound, is more and more widely used in various fields.

Reference£º
Article; Zhang, Xin; Wang, Haiying; Yuan, Jiali; Guo, Shuai; Transition Metal Chemistry; vol. 42; 8; (2017); p. 727 – 738;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17261-28-8,2-(Diphenylphosphino)benzoic acid,as a common compound, the synthetic route is as follows.

17261-28-8, Thus, crotonaldehyde was treated with HCN in the presence of an (R)-oxynitrilase readily obtained from grinding and scouring of bitter almonds,18 which gave the (R)-cyanohydrin with high levels of enantioselectivity (>96percent ee).19 Subjecting to the conditions of a Pinner reaction furnished the ethyl ester 20 (Scheme 6).20 The reduction with lithium aluminum hydride led to diol 21 and subsequent silylation furnished the silylether 22 on a multigram scale.21 Applying the standard Steglich esterification protocol22 with ortho-diphenylphosphanylbenzoic acid (o-DPPBA)23 provided o-DPPB-ester (R)-(+)-6 quantitatively. Crystallization of this product improved the enantiopurity to greater than 99percent ee. In order to obtain the requested (S)-enantiomer of 6 one could apply a corresponding (S)-oxynitrilase. However, such enzymes are far more difficult to access.24 Hence, we looked at a Mitsunobu inversion protocol, which ideally would use o-DPPBA itself as the nucleophile.25 Since o-DPPBA is both a carboxylic acid and a phosphine we expected this to be a non trivial reaction because the reagent triphenylphosphine as well as o-DPPBA may react with the azodicarboxylate electrophile. Interestingly, we observed a clean Mitsunobu reaction of the allylic alcohol 22 with o-DPPBA to furnish the corresponding (S)-(-)-enantiomer of o-DPPB-ester 6 in good yield (81percent). After recrystallization (S)-(-)-6 was obtained in >99percent enantiopurity.

The synthetic route of 17261-28-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Albert-Ludwigs-Universitat Freiburg; US2011/282075; (2011); A1;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17261-28-8,2-(Diphenylphosphino)benzoic acid,as a common compound, the synthetic route is as follows.

3-Amino-2-naphthol (0.159 g, 1.0 mmol), 2-(diphenylphosphino)benzoic acid (0.306 g,1.0 mmol) and p-toluene sulfonic acid (0.190 g, 1.0 mmol) were added to toluene (30 mL).The mixture was heated to 150C for 15 hr under nitrogen. The progress of reaction wasmonitored by TLC. After the reaction mixture cooled, the solution was extracted withwater, and the organic solution was evaporated. Then the crude intermediate in 10 mLdichloromethane were stirred in a round-bottom flask, and then H2O2 (1.2 mL, 10 mmol,30percent) was slowly added into the mixture while stirring at room temperature. The organic layer was separated and washed with water. The extract was evaporated to dryness affordinga pale yellow solid. The residue was dissolved in CHCl3 and added to methanol in orderto get solid precipitate. The crude product was purified by column chromatography withCHCl3: ethyl acetate (5:1) eluent to afford pale yellow solid (0.222 g, yield 50percent)., 17261-28-8

As the paragraph descriping shows that 17261-28-8 is playing an increasingly important role.

Reference£º
Article; Kim, Ik-Hwan; Kang, Eunguk; Kim, Dong-Eun; Shin, Hoon-Kyu; Lee, Burm-Jong; Molecular Crystals and Liquid Crystals; vol. 597; 1; (2014); p. 88 – 94;,
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

17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round bottom flask were added 2-(diphenylphosphino)benzoic acid (17.94 mg, 0.058 mmol) and 3 mL of DMF. To the solution were added 1-O-(N,N’,N,N’tetramethyluronium)azabenzotriazoloxy hexafluorophosphate (26.73 mg, 0.070 mmol), 1-hydroxyazabenzotriazole (9.56 mg, 0.070 mmol), and diisopropylethylamine (45.4 mg, 0.0612 mL). After stirring the reaction mixture for 7 minutes, N-alpha-(6-(2-(2-sulfonatobenzaldehyde)hydrazono)nicotinyl)lysine methyl ester hydrochloride (35.2 mg, 0.070 mmol) dissolved in 4 ml of DMF was added to the above mixture. The reaction mixture was stirred for 2 hours. The solvent was removed in vacuo and the resulting crude oil was subjected to HPLC purification using the method described above. The collected fractions were combined, and were lyophilized to give the product as a pale yellow solid. The yield was 29 mg (66percent) after HPLC purification., 17261-28-8

As the paragraph descriping shows that 17261-28-8 is playing an increasingly important role.

Reference£º
Patent; Liu, Shuang; US2005/8575; (2005); A1;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17261-28-8,2-(Diphenylphosphino)benzoic acid,as a common compound, the synthetic route is as follows.

Triphenylphosphonium bromide 2b (16.81 g, 49.0 mmol), and xylene (50 mL) were added into flask A (250 mL) with an inlet connected to a nitrogen balloon. To flask B (500 mL, three-necked) with an inlet connected to the flask A, (2-diphenylphosphino)benzoic acid 2e (10.00 g, 32.6 mmol), and MTBE (200 mL) were added. The flask A was heated in an oil-bath at 130 ¡ãC, and the generated HBr1 was introduced through a glass tube into the flask B under stirring by purging nitrogen. After solid 2b was completely disappeared, the reaction mixture in the flask B was filtered,and the white solids were washed with MTBE (80 mL ¡Á 2) and hexane (60 mL ¡Á 3). The solids were collected and dried in vacuo to afford (2-carboxyphenyl)diphenylphosphonium bromide 2d (11.21 g) in 89percent yield., 17261-28-8

As the paragraph descriping shows that 17261-28-8 is playing an increasingly important role.

Reference£º
Article; Huang, Wenhua; Xu, Ning; Synthetic Communications; vol. 47; 22; (2017); p. 2133 – 2138;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17261-28-8,2-(Diphenylphosphino)benzoic acid,as a common compound, the synthetic route is as follows.

17261-28-8, Thus, crotonaldehyde was treated with HCN in the presence of an (R)-oxynitrilase readily obtained from grinding and scouring of bitter almonds,18 which gave the (R)-cyanohydrin with high levels of enantioselectivity (>96percent ee).19 Subjecting to the conditions of a Pinner reaction furnished the ethyl ester 20 (Scheme 6).20 The reduction with lithium aluminum hydride led to diol 21 and subsequent silylation furnished the silylether 22 on a multigram scale.21 Applying the standard Steglich esterification protocol22 with ortho-diphenylphosphanylbenzoic acid (o-DPPBA)23 provided o-DPPB-ester (R)-(+)-6 quantitatively. Crystallization of this product improved the enantiopurity to greater than 99percent ee. In order to obtain the requested (S)-enantiomer of 6 one could apply a corresponding (S)-oxynitrilase. However, such enzymes are far more difficult to access.24 Hence, we looked at a Mitsunobu inversion protocol, which ideally would use o-DPPBA itself as the nucleophile.25 Since o-DPPBA is both a carboxylic acid and a phosphine we expected this to be a non trivial reaction because the reagent triphenylphosphine as well as o-DPPBA may react with the azodicarboxylate electrophile. Interestingly, we observed a clean Mitsunobu reaction of the allylic alcohol 22 with o-DPPBA to furnish the corresponding (S)-(-)-enantiomer of o-DPPB-ester 6 in good yield (81percent). After recrystallization (S)-(-)-6 was obtained in >99percent enantiopurity.

17261-28-8 2-(Diphenylphosphino)benzoic acid 87021, achiral-phosphine-ligands compound, is more and more widely used in various fields.

Reference£º
Patent; Albert-Ludwigs-Universitat Freiburg; US2011/282075; (2011); A1;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17261-28-8,2-(Diphenylphosphino)benzoic acid,as a common compound, the synthetic route is as follows.

DCM-OH was obtained following the previous method [48], andthen DCM-P was synthesized as outlined in Scheme 2. DCM-OH (50 mg,0.16 mmol) and 2-(diphenylphosphino)benzoic acid (161.7 mg,0.528 mmol) were dissolved in dichloromethane, then 4-(dimethylamino)-pyridinium-4-toluene sulfonate (141.3 mg, 0.48 mmol) and N,N?-diisopropylcarbodiimide (60.6 mg, 0.48 mmol) were added. The reactionsystem was stirred at room temperature for 5 h under argon protection.After the reaction was over, the mixture was extracted withdichloromethane for 3 times. The organic layer was combined and driedwith anhydrous Na2SO4, and then the solvent was evaporated in vacuo.The residual was purified by silica gel chromatography with EA/PE toget the desired product DCM-P (40 mg, 0.067 mmol), and the yield was42%. 1H NMR (400 MHz, d6-DMSO, ppm): delta 8.74 (d, J=8.1 Hz, 1H), delta8.25 (dd, J1=8.1 Hz, J2=4.0 Hz, 1H), delta 7.96-7.92 (m, 1H), delta 7.79 (d,J=12.1 Hz, 3H), delta 7.74 (s, 1H), delta 7.65-7.59 (m, 3H), delta 7.54 (d,J=16.2 Hz, 2H), delta 7.42-7.40 (m, 5H), delta 7.25-7.21 (m, 4H), delta 7.09 (d,J=8.1 Hz, 2H), delta 7.06 (d, J=8.1 Hz, 1H), delta 6.94-6.90 (m, 1H); 13CNMR (100 MHz, d6-DMSO, ppm): delta 170.79, 165.10, 158.40, 153.50,152.52, 152.04, 140.78, 140.50, 137.91, 137.65, 137.53, 135.98,134.13, 133.92, 133.41, 131.90, 131.59, 129.81, 129.51, 129.30,129.23, 126.70, 125.16, 122.84, 122.80, 120.47, 119.57, 117.58,116.23, 61.05, 60.21; HRMS (ESI, m/z): [M + H]+ calcd forC39H26N2O3P: 601.1675, Found: 601.1676 (Figure S1)., 17261-28-8

The synthetic route of 17261-28-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Tianlin; Chai, Yun; Chen, Shuhan; Yang, Guichun; Lu, Cuifen; Nie, Junqi; Ma, Chao; Chen, Zuxing; Sun, Qi; Zhang, Yuexing; Ren, Jun; Wang, Feiyi; Zhu, Wei-Hong; Dyes and Pigments; vol. 166; (2019); p. 260 – 265;,
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

17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compounds 1d? was prepared according to the reported procedures.2 The 1d? (320 mg, 1 mmol) was dissolved in CH2Cl2 (10 mL) and trifluoroacetic acid (1 ml) was dropwise added at 0 ¡ãC. Then the reaction mixture was stirred for 18 h at room temperature. All volatile compounds were removed invacuo and the residue was dissolved in water and treated with the saturated Na2CO3 solution. The resulting mixture was extracted with CH2Cl2 (3x) and the combined organic layers were dried over Na2SO4. After filtration and then evaporation of the solvent, the crude free amine was obtained without purification for the next step. To the solution of the free amine in CH2Cl2 (8 ml) was added O-benztriazole-1-N,N,N?,N?-tetraethyluronium hexafluorophosphate (HBTU, 417 mg, 1.1 mmol),followed by the addition of diisopropylethylamine (367 uL, 2.2 mmol) and 2-(diphenylphosphino)benzoic acid (306 mg, 1 mmol), The reaction mixture was then stirred for 18 h at room temperature. The mixture was combined with CH2Cl2 and water, and the organic layer was separated, washed with saturated sodium bicarbonate (2x), and dried over Na2SO4. The solvent was removed in vacuo to afford the crude product as colourless oil, which was purified by flash chromatography (15percent EtOAc in hexanes) yielding the precat 1d (356 mg, 70percent), 17261-28-8

As the paragraph descriping shows that 17261-28-8 is playing an increasingly important role.

Reference£º
Article; Zhou, Zhipeng; Zheng, Xiaojun; Liu, Jialin; Li, Jinlei; Wen, Pushan; Wang, Haifei; Synlett; vol. 28; 8; (2017); p. 999 – 1003;,
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

17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

17261-28-8, 2-(Diphenylphosphanyl)benzoic acid (0.50 g, 1.63 mmol) and DMAP (20 mg, 0.163 mmol) were dissolved in CH2Cl2 (10 mL). Ethanethiol (EtSH, 0.35 mL, 4.89 mmol) was added, and the solution was placed under Ar(g) and cooled to 0¡ã C. DIC (0.25 mL, 1.63 mmol) was added dropwise, and the resulting solution was allowed to warm to room temperature and stirred overnight. The solution was then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with 10percent EtOAc/hexanes, to give phosphine 1b as a pale yellow solid (0.43 g, 1.22 mmol, 75percent yield).Data for 1b: 1H NMR (400 MHz, CDCl3) delta=8.02 (m, 1H, Ar.), 7.45-7.24 (m, 12H, Ar.), 6.99 (m, 1H, Ar.), 2.98 (q, 2H, J=7.4 Hz, SCH2CH3), 1.22 (t, 3H, J=7.4 Hz, SCH2CH3). 13C NMR (100 MHz, CDCl3, 31P-coupled; 1H-decoupled, observed signals) delta=192.7, 141.9, 141.7, 138.0, 137.8, 137.7, 134.6, 134.0, 133.8, 131.7, 128.9, 128.6, 128.4, 128.4, 128.3, 24.0, 14.6. 31P NMR (162 MHz, CDCl3) delta=-5.8. HRMS (ESI+) m/z calculated for (C21H20OPS)+ 351.0968, measured 351.0953.

The synthetic route of 17261-28-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Raines, Ronald Thaddeus; Myers, Eddie Leonard; US2010/125132; (2010); A1;,
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

17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

17261-28-8, A mixture of NBD-Cl (400 mg, 2 mmol) and 2-(methylamino) ethan-1-ol (200 mL, 2.5 mmol) was dissolved in20 mL CH2Cl2, and then DIPEA (430 mL, 2.5 mmol) was added. Thereaction mixture and stirred at room temperature for 2 h. Themixture was washed by water (3 25 mL) and brine, and dried byNa2SO4. After removing the solvent under reduced pressure, theresidue was purified by silica gel column chromatography to give ared solid 3a (138 mg, 29%). 1H NMR (400 MHz, MeOD) d 8.54 (d,J 9.1 Hz, 1H), 6.44 (d, J 9.1 Hz, 1H), 4.33 (s, 2H), 3.95 (t, J 5.5 Hz,2H), 3.62 (s, 3H). 2-(Diphenylphosphanyl) benzoic acid (123 mg,0.41 mmol), EDC (84 mg, 0.44 mmol) and DMAP (54 mg,0.44 mmol) were dissolved by CH2Cl2, and then 3a (80 mg,0.34 mmol) was added. The mixture was stirred at room temperatureunder nitrogen protection overnight. After removing thesolvent under reduced pressure, the resulting residue was purifiedby silica gel column chromatography with CH2Cl2 to get an orangefoam 3 (146 mg, 87%). 1H NMR (400 MHz, CDCl3) d 8.36 (d,J 8.9 Hz, 1H), 7.78 (s, 1H), 7.34 (dt, J 10.8, 6.1 Hz, 8H), 7.21 (dd,J 10.4, 4.9 Hz, 4H), 6.91 (s, 1H), 6.04 (d, J 9.0 Hz, 1H), 4.52 (t,J 5.3 Hz, 2H), 4.37 (s, 2H), 3.35 (s, 3H). 13C NMR (101 MHz, CDCl3)d 166.4, 145.42 (s), 144.7, 140.97 (s), 140.7, 137.5, 135.2, 134.6, 134.0,133.8,133.3,133.1,132.6,130.5,128.9,128.6,128.4,123.2,102.0, 62.2,54.2, 41.9. 31P NMR (162 MHz, DMSO-d6) d 4.37. HRMS (ESI): m/z[MH] calcd. for C28H24N4O5P: 527.1479; found: 527.1488.

The synthetic route of 17261-28-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ma, Dejun; Kang, Xueying; Gao, Yasi; Zhu, Jiqin; Yi, Long; Xi, Zhen; Tetrahedron; vol. 75; 7; (2019); p. 888 – 893;,
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