(R,Z)-2-cyano-5-(4-methoxy-phenyl)-5-oxo-2-phenyl-pent-3-enoic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,Z)-2-cyano-5-(4-methoxy-phenyl)-5-oxo-2-phenyl-pent-3-enoic acid tert-butyl ester
• 英文别名: tert-butyl (Z,2R)-2-cyano-5-(4-methoxyphenyl)-5-oxo-2-phenylpent-3-enoate
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: PZMUNRDOOLUCKW-SYKNXGGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-chloro-1-(4-methoxy-phenyl)-propenone 、 2-叔丁氧羰基-2-苯基乙腈 在 dimeric cinchonine-derived compound 、 caesium carbonate 作用下， 以 氯仿 、 水 为溶剂， 生成 (E)-2-cyano-5-(4-methoxy-phenyl)-5-oxo-2-phenyl-pent-3-enoic acid tert-butyl ester 、 (S,Z)-2-cyano-5-(4-methoxy-phenyl)-5-oxo-2-phenyl-pent-3-enoic acid tert-butyl ester 、 (R,Z)-2-cyano-5-(4-methoxy-phenyl)-5-oxo-2-phenyl-pent-3-enoic acid tert-butyl ester
  参考文献：
  名称：

  Organocatalytic Enantioselective Nucleophilic Vinylic Substitution by α-Substituted-α-Cyanoacetates under Phase-Transfer Conditions

  摘要：

  The organocatalytic enantioselective formation of vinyl-substituted all-carbon quaternary stereocenters via nucleophilic vinylic substitution by alpha-substituted-alpha-cyanoacetates is presented. The reaction proceeds well for different alpha-substituted-alpha-cyanoacetates and beta-chloroalkenones using a dimeric cinchona alkaloid phase-transfer catalyst giving the products in good yield and with enantioselectivities up to 98% ee.

  DOI：

  10.1021/jo070024p

文献信息

• Organocatalytic Enantioselective Nucleophilic Vinylic Substitution by α-Substituted-α-Cyanoacetates under Phase-Transfer Conditions
  作者：Mark Bell、Thomas B. Poulsen、Karl Anker Jørgensen

  DOI：10.1021/jo070024p

  日期：2007.4.1

  The organocatalytic enantioselective formation of vinyl-substituted all-carbon quaternary stereocenters via nucleophilic vinylic substitution by alpha-substituted-alpha-cyanoacetates is presented. The reaction proceeds well for different alpha-substituted-alpha-cyanoacetates and beta-chloroalkenones using a dimeric cinchona alkaloid phase-transfer catalyst giving the products in good yield and with enantioselectivities up to 98% ee.