methyl (2R,3R)-2-chloro-3-hydroxy-3-phenylpropanoate | 1245930-50-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2R,3R)-2-chloro-3-hydroxy-3-phenylpropanoate
• 英文别名: methyl (R,R)-2-chloro-3-hydroxy-3-phenylpropanoate
• CAS: 1245930-50-0
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: OXWHLUNHUCVJKF-RKDXNWHRSA-N

物化性质

• 沸点：
  348.5±37.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R)-2-chloro-3-hydroxy-3-phenylpropanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到methyl trans-3-phenylglycidate
  参考文献：
  名称：

  Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation

  摘要：

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.017
• 作为产物：
  描述：

  2-氯-3-氧代-3-苯基丙酸甲酯 在 [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 50.0 ℃ 、6.0 MPa 条件下， 反应 48.0h， 生成 methyl (2R,3R)-2-chloro-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation

  摘要：

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.017

文献信息

• Triethylamine-promoted Elimination from (R,R)-PhCHORCHClCO2Me (R=MeCO, PhCO, 4-MeC6H4, 4-MeOC6H4, MeSO2 and 4-MeC6H4SO2) in Various Solvents
  作者：Rosana S. Montani、Elisabet Gil、Mercedes C. Cabaleiro

  DOI：10.1039/a806946h

  日期：——

  The rates and stereochemistry of elimination from a number of (R,R)-PhCHORCHClCO2Me (R=MeCO, PhCO, 4-MeC6H4, 4-MeOC6H4, MeSO2 and 4-MeC6H4SO2) with triethylamine in tetrahydrofuran, acetone, methanol, dimethylformamide and acetonitrile as solvents led to the conclusion that the elimination process occurs through an (E1cB)I mechanism.

  在四氢呋喃、丙酮、甲醇、二甲基甲酰胺和乙腈中使用三乙胺从许多 (R,R)-PhCHORCHClCO2Me（R=MeCO、PhCO、4-MeC6H4、4-MeOC6H4、MeSO2 和 4-MeC6H4SO2）中消除的速率和立体化学作为溶剂导致的结论是消除过程是通过 (E1cB)I 机制发生的。
• Enantioselective ruthenium-mediated hydrogenation: developments and applications
  作者：Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/s0022-328x(98)00680-9

  日期：1998.9

  A general preparation of chiral ruthenium(II) catalysts and the homogeneous enantioselective hydrogenation of prochiral olefins and keto groups are presented. Some applications to the synthesis of biologically active compounds are reported. (C) 1998 Elsevier Science S.A. All rights reserved.
• Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation
  作者：Sébastien Prévost、Sébastien Gauthier、Maria Cristina Caño de Andrade、Céline Mordant、Ali Rhida Touati、Philippe Lesot、Philippe Savignac、Tahar Ayad、Phannarath Phansavath、Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/j.tetasy.2010.05.017

  日期：2010.6

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.