ethyl (R)-3-hydroxy-4,4-dichlorobutyrate | 166896-26-0

• 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: ethyl (R)-3-hydroxy-4,4-dichlorobutyrate
• 英文别名: ethyl (3R)-4,4-dichloro-3-hydroxybutanoate
• CAS: 166896-26-0
• 化学式: C₆H₁₀Cl₂O₃
• 分子量: 201.05
• InChiKey: ITXCETQCXQNPCC-SCSAIBSYSA-N

物化性质

• 沸点：
  292.4±35.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate 在 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到ethyl (R)-3-hydroxy-4,4-dichlorobutyrate
  参考文献：
  名称：

  New method for the preparation of (R)-carnitine

  摘要：

  A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate [(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].

  DOI：

  10.1016/0957-4166(95)00125-9

文献信息

• Preparation of Ethyl (<i>R</i>)-3-hydroxy-4-chlorobutyrate by Selective Reduction of (<i>R</i>)-4-(Trichloromethyl)-oxetan-2-one: Key Intermediate to (<i>R</i>)-Carnitine and (<i>R</i>)-4-Amino-3-hydroxybutyric Acid
  作者：Choong Eui Song、Jae Kyun Lee、In O Kim、Jung Hoon Choi

  DOI：10.1080/00397919708003044

  日期：1997.3

  Selective reduction of (R)-4-(trichloromethyl)-oxetan-2-one in ethanol by catalytic hydrogenation on Pd-C in the presence of KOAc gave directly ethyl (R)-3-hydroxy-4-chlorobutyrate, which can be used as a key intermediate for the synthesis of some biblogically active gamma-amino-beta-hydroxy amino acids, (R)-carnitine and gamma-amino-beta-hydroxy amino acid ((R)-GABOB).
• New method for the preparation of (R)-carnitine
  作者：Choong Eui Song、Jae Kyun Lee、So Ha Lee、Sang-gi Lee

  DOI：10.1016/0957-4166(95)00125-9

  日期：1995.5

  A new method for the preparation of (R)-carnitine (1) has been developed from enantiomerically pure (R)-4-(trichloromethyl)-oxetan-2-one [(R)-2] which was easily obtained from the [2+2]-cycloaddition of ketene and chloral in the presence of catalytic amounts of poly(acryloyl quinidine). The key intermediate, ethyl (R)-3-hydroxy-4-chlorobutyrate [(R)-5], was prepared by ethanolysis of (R)-2 followed by selective bis-dechlorination of ethyl (R)-3-hydroxy-4,4,4-trichlorobutyrate [(R)-3].