(Z)-ethyl 4-carbomethoxy-4-cyclohexyl-2-butenoate | 120780-34-9

• 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: (Z)-ethyl 4-carbomethoxy-4-cyclohexyl-2-butenoate
• 英文别名: 1-O-ethyl 5-O-methyl (Z)-4-cyclohexylpent-2-enedioate
• CAS: 120780-34-9
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: WITLSDVEUYEABO-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ((2-环己基-1-甲氧基乙烯基)氧基)三甲基硅烷 、 丙炔酸乙酯 在 水 、 四氯化钛 作用下， 生成 (Z)-ethyl 4-carbomethoxy-4-cyclohexyl-2-butenoate 、 (E)-ethyl 4-carbomethoxy-4-cyclohexyl-2-butenoate
  参考文献：
  名称：

  Preparation and reactivity of the adducts of ketene alkylsilyl acetals with ethyl propiolate in the presence of titanium tetrachloride

  摘要：

  The reaction of ketene alkylsilyl acetals with ethyl propiolate in the presence of TiCl4 led to intermediates whose reactivity was studied with electrophiles such as H2O, D2O, NBS, NCS, and PhSeCl to form glutaconate derivatives. Except in the case of the dimethylketene trimethylsilyl acetal, for which the reaction was stereospecific, with other ketene acetals the selectivity was lower. Similar results were observed in the reaction of these titanium intermediates with aldehydes and ketones. The results were interpretated as the formation of vinylic titanium intermediates (more stabilized in the case of the dimethylketene acetal) in equilibrium with the titanium allenolates.

  DOI：

  10.1021/jo00051a039

文献信息

• Reaction of ketenealkylsilylacetals with ethyl propiolate
  作者：A. Quendo、G. Rousseau

  DOI：10.1016/s0040-4039(00)82368-0

  日期：1988.1

  The reaction of ketenealkylsilylacetals with ethyl propiolate in the presence of different Lewis acids is reported to give Michaël-type additions or a [2+2] cycloaddition.

  据报道，在不同的路易斯酸存在下，烯酮烷基甲硅烷基缩醛与丙酸乙酯的反应产生了Michaël型加成或[2 + 2]环加成。
• Preparation and reactivity of the adducts of ketene alkylsilyl acetals with ethyl propiolate in the presence of titanium tetrachloride
  作者：Alain Quendo、Syed Massarat Ali、Gerard Rousseau

  DOI：10.1021/jo00051a039

  日期：1992.12

  The reaction of ketene alkylsilyl acetals with ethyl propiolate in the presence of TiCl4 led to intermediates whose reactivity was studied with electrophiles such as H2O, D2O, NBS, NCS, and PhSeCl to form glutaconate derivatives. Except in the case of the dimethylketene trimethylsilyl acetal, for which the reaction was stereospecific, with other ketene acetals the selectivity was lower. Similar results were observed in the reaction of these titanium intermediates with aldehydes and ketones. The results were interpretated as the formation of vinylic titanium intermediates (more stabilized in the case of the dimethylketene acetal) in equilibrium with the titanium allenolates.