(E)-4-Methyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester | 185562-74-7

• 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)-4-Methyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester
• 英文别名: methyl (E)-4-methyl-4-(4-methylphenyl)sulfonylpent-2-enoate
• CAS: 185562-74-7
• 化学式: C₁₄H₁₈O₄S
• 分子量: 282.361
• InChiKey: HPVYLXBXFLMSMW-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲基丙二酸钠 、 (E)-4-Methyl-4-(toluene-4-sulfonyl)-pent-2-enoic acid methyl ester 在 四(三苯基膦)钯 作用下， 生成 (E)-5-Methoxycarbonyl-4,4-dimethyl-hex-2-enedioic acid dimethyl 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
• 作为产物：
  描述：

  (E)-methyl-4-(tosyl)but-2-enoate 、 碘甲烷 在 sodium hydride 作用下， 生成 (E)-4-Methyl-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