(2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester | 164334-44-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester
• 英文别名: 1-O-tert-butyl 5-O-propan-2-yl (2S,3S)-2-[(E,1S,2R)-4-[(3aR,7aR)-1,3-dimethyl-2-oxo-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-yl]-2-methyl-1-phenylbut-3-enyl]-3-phenylpentanedioate
• CAS: 164334-44-5
• 化学式: C₃₇H₅₃N₂O₅P
• 分子量: 636.812
• InChiKey: GPNYTPLKURDSPT-JOADODKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-3-phenyl-pentanedioic acid 1-tert-butyl ester 5-isopropyl ester 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,3S)-2-((1S,2R)-2-Methyl-3-oxo-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 、 Lithium; (1Z,5E)-(3S,4R)-1-tert-butoxy-6-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-4-methyl-3-phenyl-hexa-1,5-dien-1-olate 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以52%的产率得到(2S,3S)-2-[(E)-(1S,2R)-4-((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-2-methyl-1-phenyl-but-3-enyl]-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