(E)-2-Benzyl-5-phenyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester | 185562-87-2

• 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: (E)-2-Benzyl-5-phenyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester
• CAS: 185562-87-2
• 化学式: C₂₆H₂₆O₄S
• 分子量: 434.556
• InChiKey: NLGPODHUZAWQJK-FCDQGJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Benzyl-5-phenyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以80%的产率得到
  参考文献：
  名称：

  Studies on the reactivity of methyl γ-tosylcrotonoate as ambident reagent in organic synthesis

  摘要：

  The treatment of methyl O-4-tosyl-2-butenoate (4) with two equiv. of sodium hydride and different mono and dihalides gives mainly gamma,gamma- and alpha,alpha- or alpha,gamma- and alpha,alpha-dialkylated products (5-7) depending on the electrophile. The corresponding monoanion dimerizes with iodine to afford stereoselectively dimethyl cis-4,5-ditosyl-2,2,6-cyclohexadiene-1,2-dicarboxylate (11). The tosyl group in compounds 6 and 7 is reduced and in the case of gamma,gamma-dimethylated 5a substituted by sodium dimethyl malonate under Pd(PPh(3))(4) catalysis. Michael addition of different nucleophiles provides the corresponding beta-substituted methyl gamma-tosylbutanoates 16. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00929-5
• 作为产物：
  描述：

  4-溴-2-丁烯酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 49.0h， 生成 (E)-2-Benzyl-5-phenyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Studies on the reactivity of methyl γ-tosylcrotonoate as ambident reagent in organic synthesis

  摘要：

  The treatment of methyl O-4-tosyl-2-butenoate (4) with two equiv. of sodium hydride and different mono and dihalides gives mainly gamma,gamma- and alpha,alpha- or alpha,gamma- and alpha,alpha-dialkylated products (5-7) depending on the electrophile. The corresponding monoanion dimerizes with iodine to afford stereoselectively dimethyl cis-4,5-ditosyl-2,2,6-cyclohexadiene-1,2-dicarboxylate (11). The tosyl group in compounds 6 and 7 is reduced and in the case of gamma,gamma-dimethylated 5a substituted by sodium dimethyl malonate under Pd(PPh(3))(4) catalysis. Michael addition of different nucleophiles provides the corresponding beta-substituted methyl gamma-tosylbutanoates 16. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00929-5

文献信息

• Studies on the reactivity of methyl γ-tosylcrotonoate as ambident reagent in organic synthesis
  作者：Francisco Caturla、Carmen Nájera

  DOI：10.1016/s0040-4020(96)00929-5

  日期：1996.11

  The treatment of methyl O-4-tosyl-2-butenoate (4) with two equiv. of sodium hydride and different mono and dihalides gives mainly gamma,gamma- and alpha,alpha- or alpha,gamma- and alpha,alpha-dialkylated products (5-7) depending on the electrophile. The corresponding monoanion dimerizes with iodine to afford stereoselectively dimethyl cis-4,5-ditosyl-2,2,6-cyclohexadiene-1,2-dicarboxylate (11). The tosyl group in compounds 6 and 7 is reduced and in the case of gamma,gamma-dimethylated 5a substituted by sodium dimethyl malonate under Pd(PPh(3))(4) catalysis. Michael addition of different nucleophiles provides the corresponding beta-substituted methyl gamma-tosylbutanoates 16. Copyright (C) 1996 Elsevier Science Ltd