(2R,3S)-2-((S)-3-Hydroxy-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester | 164334-45-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2R,3S)-2-((S)-3-Hydroxy-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester
• 英文别名: 1-O-tert-butyl 5-O-propan-2-yl (2R,3S)-2-[(1S)-3-hydroxy-1-phenylpropyl]-3-phenylpentanedioate
• CAS: 164334-45-6
• 化学式: C₂₇H₃₆O₅
• 分子量: 440.58
• InChiKey: GXDYOPLXXNXDDZ-VDKIKQQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((S)-3-Hydroxy-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester 在 四溴化碳 、 三苯基膦 作用下， 以81%的产率得到(2S,3S)-2-((S)-3-Bromo-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester
  参考文献：
  名称：

  Highly stereocontrolled sequential asymmetric Michael addition reactions with cinnamate esters - generation of three and four contiguous stereogenic centers on seven-carbon acyclic motifs

  摘要：

  The reaction of allyl and crotyl bicyclic chiral phosphonamide anions with two cinnamate esters leads to a sequential Michael reaction with excellent diastereoselectivity. The option to quench enolates with methyl iodide greatly enhances the versatility of the reaction in the synthesis of acyclic seven-carbon chains with vicinal and alternating C-methyl and C-phenyl substituents.

  DOI：

  10.1016/s0040-4039(00)78330-4
• 作为产物：
  描述：

  (E)-isopropyl cinnamate 在 sodium tetrahydroborate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,3S)-2-((S)-3-Hydroxy-1-phenyl-propyl)-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester
  参考文献：
  名称：

  Highly stereocontrolled sequential asymmetric Michael addition reactions with cinnamate esters - generation of three and four contiguous stereogenic centers on seven-carbon acyclic motifs

  摘要：

  The reaction of allyl and crotyl bicyclic chiral phosphonamide anions with two cinnamate esters leads to a sequential Michael reaction with excellent diastereoselectivity. The option to quench enolates with methyl iodide greatly enhances the versatility of the reaction in the synthesis of acyclic seven-carbon chains with vicinal and alternating C-methyl and C-phenyl substituents.

  DOI：

  10.1016/s0040-4039(00)78330-4

文献信息

• Highly stereocontrolled sequential asymmetric Michael addition reactions with cinnamate esters - generation of three and four contiguous stereogenic centers on seven-carbon acyclic motifs
  作者：Stephen Hanessian、Arthur Gomtsyan

  DOI：10.1016/s0040-4039(00)78330-4

  日期：1994.10

  The reaction of allyl and crotyl bicyclic chiral phosphonamide anions with two cinnamate esters leads to a sequential Michael reaction with excellent diastereoselectivity. The option to quench enolates with methyl iodide greatly enhances the versatility of the reaction in the synthesis of acyclic seven-carbon chains with vicinal and alternating C-methyl and C-phenyl substituents.