methyl (2R,3S)-(+)-3-(4-chlorophenylamino)-2-hydroxy-3-phenylpropanoate | 945548-79-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R,3S)-(+)-3-(4-chlorophenylamino)-2-hydroxy-3-phenylpropanoate
• 英文别名: methyl (2R,3S)-3-(4-chloroanilino)-2-hydroxy-3-phenylpropanoate
• CAS: 945548-79-8
• 化学式: C₁₆H₁₆ClNO₃
• 分子量: 305.761
• InChiKey: RIIUXSZUKJJKOX-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-(+)-3-(4-chlorophenylamino)-2-hydroxy-3-phenylpropanoate 、 二甲基亚砜 在 四磷十氧化物 作用下， 反应 24.17h， 以95%的产率得到methyl (4S,5R)-(+)-3-(4-chlorophenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of oxazolidines using DMSO/P4O10 as a formaldehyde equivalent

  摘要：

  Compounds containing a substituted oxazolidine ring were prepared in excellent yields in two steps from cis or trans 3-phenylglycidate. When an electron donating amine was used in the nucleophilic opening of an epoxide, treatment of the resulting beta-amino-alpha-hydroxy ester with DMSO/P4O10 led to the formation of cis or trans oxazolidines. This simple and practical procedure was readily adapted to the synthesis of enantiopure oxazolidines, using DMSO/P4O10 because of the availability of the enantiopure halohydrins from enzymatic reduction of the beta-chloro-alpha-ketoester. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.017
• 作为产物：
  描述：

  methyl 3-phenyl-3-chloro-2-ketopropionate 在 D-glucose dehydrogenase 葡萄糖 、 potassium carbonate 、 还原型辅酶II(NADPH)四钠盐 、 zinc(II) chloride 作用下， 以 phosphate buffer 、 二甲基亚砜 、 乙腈 为溶剂， 反应 12.0h， 生成 methyl (2R,3S)-(+)-3-(4-chlorophenylamino)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of oxazolidines using DMSO/P4O10 as a formaldehyde equivalent

  摘要：

  Compounds containing a substituted oxazolidine ring were prepared in excellent yields in two steps from cis or trans 3-phenylglycidate. When an electron donating amine was used in the nucleophilic opening of an epoxide, treatment of the resulting beta-amino-alpha-hydroxy ester with DMSO/P4O10 led to the formation of cis or trans oxazolidines. This simple and practical procedure was readily adapted to the synthesis of enantiopure oxazolidines, using DMSO/P4O10 because of the availability of the enantiopure halohydrins from enzymatic reduction of the beta-chloro-alpha-ketoester. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.017