ethyl 1-<2-(ethoxycarbonyl)-2-methoxy-1-ethenyl>-2-methoxy-2-<(trimethylsilyl)oxy>cyclopent-3-ene-1-carboxylate | 136175-71-8

• 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: ethyl 1-<2-(ethoxycarbonyl)-2-methoxy-1-ethenyl>-2-methoxy-2-<(trimethylsilyl)oxy>cyclopent-3-ene-1-carboxylate
• CAS: 136175-71-8
• 化学式: C₁₈H₃₀O₇Si
• 分子量: 386.518
• InChiKey: WNESIQTXWYYWJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-<2-(ethoxycarbonyl)-2-methoxy-1-ethenyl>-2-methoxy-2-<(trimethylsilyl)oxy>cyclopent-3-ene-1-carboxylate 在 水 作用下， 生成 1-((Z)-2-Ethoxycarbonyl-2-methoxy-vinyl)-2-oxo-cyclopent-3-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene

  摘要：

  Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

  DOI：

  10.1021/jo00022a041
• 作为产物：
  描述：

  1-(trimethylsiloxy)-1-methoxy-1,3-butadiene 、 2-diazonio-1,5-diethoxy-4-methoxy-5-oxopenta-1,3-dien-1-olate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以18%的产率得到ethyl 1-<2-(ethoxycarbonyl)-2-methoxy-1-ethenyl>-2-methoxy-2-<(trimethylsilyl)oxy>cyclopent-3-ene-1-carboxylate
  参考文献：
  名称：

  Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene

  摘要：

  Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

  DOI：

  10.1021/jo00022a041