(2aα,4aα,7aα,7bα)-octahydro-2-carbomethoxyindeno<7,1-bc>furan-2-one | 120790-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2aα,4aα,7aα,7bα)-octahydro-2-carbomethoxyindeno<7,1-bc>furan-2-one
• 英文别名: (2aα,4aα,7aα,7bα)-octahydro-2a-carbomethoxyindeno<7,1-bc>furan-2-one；methyl (1S,4R,7S,11S)-3-oxo-2-oxatricyclo[5.3.1.04,11]undecane-4-carboxylate
• CAS: 120790-44-5
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: SIXVVWJPUKTFPP-APOZVJGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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-ethyl (2-cyclohexene-1-yl)) malonate de dimethyle 在 titanium(IV) tetrabutoxide 、 碘 作用下， 生成 (2aα,4aα,7aα,7bα)-octahydro-2-carbomethoxyindeno<7,1-bc>furan-2-one
  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

• Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures
  作者：Dennis P. Curran、Chi Tai Chang

  DOI：10.1021/jo00274a034

  日期：1989.6