dimethyl <3-(1-cyclohexenyl)propyl>malonate

• 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: dimethyl <3-(1-cyclohexenyl)propyl>malonate
• 英文别名: Dimethyl 2-[3-(cyclohexen-1-yl)propyl]propanedioate
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: DZASESUQNMUFSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  8
• 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

• 作为反应物：
  描述：

  dimethyl <3-(1-cyclohexenyl)propyl>malonate 在 titanium(IV) tetrabutoxide 、 碘 作用下， 生成 (3aR,5aR,9aS)-4-Oxo-hexahydro-benzo[b]cyclopenta[c]furan-3a-carboxylic acid methyl ester
  参考文献：
  名称：

  Ionic iodocarbocyclization reactions of 4-alkenyl- and 4-alkynylmalonate derivatives

  摘要：

  The cyclization reactions of dimethyl 4-alkenylmalonate derivatives la-d in the presence Of 12 and Ti(Ot-Bu)4 proceed in a highly regio- and stereocontrolled manner (5-exo cyclization and trans addition) to give (iodoalkyl)cyclopentane derivatives 2 or bicyclic lactones 3 through the displacement of the iodide of 2 by an ester group. Iodocarbocyclization reactions of dimethyl [(cycloalkenyl)alkyl]malonates 1g-i or dimethyl [(methylenecycloalkyl)alkyl]malonates 1j and 1k proceed regio- and stereoselectively to give fused ring compounds or spiro compounds, respectively, as single isomers. Similar reactions of 4-alkynyl derivatives 5 give preferentially E-iodomethylene cyclopentane derivatives 6. An ionic mechanism rather than a radical mechanism is suggested on the basis of the regioselectivity and stereospecificity of the above reactions.

  DOI：

  10.1021/jo00063a033

文献信息

• Ionic iodocarbocyclization reactions of 4-alkenyl- and 4-alkynylmalonate derivatives
  作者：Osamu Kitagawa、Tadashi Inoue、Keiko Hirano、Takeo Taguchi

  DOI：10.1021/jo00063a033

  日期：1993.5

  The cyclization reactions of dimethyl 4-alkenylmalonate derivatives la-d in the presence Of 12 and Ti(Ot-Bu)4 proceed in a highly regio- and stereocontrolled manner (5-exo cyclization and trans addition) to give (iodoalkyl)cyclopentane derivatives 2 or bicyclic lactones 3 through the displacement of the iodide of 2 by an ester group. Iodocarbocyclization reactions of dimethyl [(cycloalkenyl)alkyl]malonates 1g-i or dimethyl [(methylenecycloalkyl)alkyl]malonates 1j and 1k proceed regio- and stereoselectively to give fused ring compounds or spiro compounds, respectively, as single isomers. Similar reactions of 4-alkynyl derivatives 5 give preferentially E-iodomethylene cyclopentane derivatives 6. An ionic mechanism rather than a radical mechanism is suggested on the basis of the regioselectivity and stereospecificity of the above reactions.