2-氯-3-羟基-3-苯基丙酸乙酯 | 146452-40-6

• 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
• 中文名称: 2-氯-3-羟基-3-苯基丙酸乙酯
• 英文名称: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate
• 英文别名: ethyl (2R,3R)-2-chloro-3-hydroxy-3-phenylpropanoate
• CAS: 146452-40-6
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: OHWTWQBFVOCYOY-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-氯-3-羟基-3-苯基丙酸乙酯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以60%的产率得到(S)-(-)-3-羟基-3-苯基丙酸乙酯
  参考文献：
  名称：

  The microbial reduction of 2-chloro-3-oxoesters

  摘要：

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.

  DOI：

  10.1016/0957-4166(95)00294-y
• 作为产物：
  描述：

  ethyl 2-chloro-3-oxo-3-phenylpropionate 在 Tween 80 、 乙醇 作用下， 反应 72.0h， 以51%的产率得到2-氯-3-羟基-3-苯基丙酸乙酯
  参考文献：
  名称：

  The microbial reduction of 2-chloro-3-oxoesters

  摘要：

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.

  DOI：

  10.1016/0957-4166(95)00294-y

文献信息

• Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions
  作者：Liqin Qiu、Jianying Qi、Cheng-Chao Pai、Shusun Chan、Zhongyuan Zhou、Michael C. K. Choi、Albert S. C. Chan

  DOI：10.1021/ol026817+

  日期：2002.12.1

  Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective

  ［结构：见正文］合成了在主链上增加了手性中心的非对映体联芳基二膦配体10和11。在非对映体二膦氧化物的制备的偶联步骤中发生了底物定向的不对称合成。通过使用硅胶的柱色谱法容易地分离非对映体二膦氧化物。含有这些配体的钌催化剂在2-（6'-甲氧基-2'-萘基）丙酸和β-酮酸酯的氢化中非常有效。额外的手性中心对催化剂的对映选择性和活性有重大影响。
• Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R,3S)-3-phenylisoserine
  作者：Odile Cabon、Didier Buisson、Marc Larcheveque、Robert Azerad

  DOI：10.1016/0957-4166(95)00295-z

  日期：1995.9

  Cis- and trans-glycidic esters may be synthesized in high enantiomeric purities by cyclisation with potassium carbonate in DMF of the corresponding syn- or anti-2-chloro-3-hydroxyesters, prepared by microbial reduction of 2-chloro-3-oxoesters. In contrast, more basic media such as sodium ethylate afford exclusively the trans-isomer, whatever the stereochemistry of the starting 2-chloro-3-hydroxyester

  顺式-和反式-缩水甘油酯可以通过在碳酸镁中将碳酸钾通过微生物还原2-氯-3-氧酸酯的方法在相应的顺式或反式-2-氯-3-羟基酯中与碳酸钾环化而合成，以高对映体纯度合成。相反，无论起始的2-氯-3-羟基酯的立体化学是什么，更多的碱性介质如乙醇钠仅提供反式异构体。氘代化合物的环化表明，该结果是由于环化之前合成酯迅速异构化为反异构体所致。该反应在合成（2 R，3 S描述了）-3-苯基异丝氨酸。
• A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes
  作者：Jean-Pierre Genêt、M.C. Caño de Andrade、V. Ratovelomanana-Vidal

  DOI：10.1016/0040-4039(95)00182-c

  日期：1995.3

  2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (Ii) catalysts prepared in-situ from (COD)Ru(2-Methylallyl)(2) in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%. 2-chloro-3-hydroxy esters were treated with different bases to give (E)- and (Z)-2,3-epoxyalkanoates in 65-90% yields with 84-97% ee.
• Microbial reduction of 2-chloro-3-aryl-3-oxopropionic acid esters
  作者：Odile Cabon、Marc Larchevêque、Didier Buisson、Robert Azerad

  DOI：10.1016/s0040-4039(00)60181-8

  日期：1992.11

  2-Chloro-3-aryl-3-oxopropionic acid esters are reduced by microorganisms to syn- and/or anti-2-chloro-3-hydroxy-3-arylpropionates, in competition with dechlorination and decarboxylation reactions. Using selected strains, it is possible to obtain enantiomerically pure chlorohydroxyesters, which were converted to the corresponding phenylglycidic esters with high stereospecificity.
• The microbial reduction of 2-chloro-3-oxoesters
  作者：Odile Cabon、Didier Buisson、Marc Larcheveque、Robert Azerad

  DOI：10.1016/0957-4166(95)00294-y

  日期：1995.9

  Several aliphatic or aromatic 2-chloro-3-oxoesters are stereoselectively reduced by yeast or fungal strains, affording in fair to good yield and high enantiomeric excess some of the respective 2-chloro-3-hydroxyester stereoisomers.

表征谱图