(2aα,2bα,5aα,5bα)-hexahydrocyclopropabenzofuran-2(2aH)-one | 123826-92-6

• 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,2bα,5aα,5bα)-hexahydrocyclopropabenzofuran-2(2aH)-one
• 英文别名: (2aα,2bα,5aα,5bα)-hexahydrocyclopropa(cd)benzofuran-2(2aH)-one；(1R,2S,6R)-7-oxatricyclo[4.3.0.02,9]nonan-8-one
• CAS: 123826-92-6；134003-38-6
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: PXTPBWTUDCILLO-KYDWDHDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2aα,2bα,5aα,5bα)-hexahydrocyclopropabenzofuran-2(2aH)-one 在 三丁基膦 、 三甲基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (1α,2α,6α,7β)-N,N-dimethyl-2-(phenylseleno)bicyclo<4.1.0>heptane-7-carboxamide
  参考文献：
  名称：

  Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals

  摘要：

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.

  DOI：

  10.1021/jo00012a009
• 作为产物：
  描述：

  2-环己烯醇 在 bis(N-tert-butylsalicylaldiminato)copper(II) N,N-二甲基苯胺 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.08h， 生成 (2aα,2bα,5aα,5bα)-hexahydrocyclopropabenzofuran-2(2aH)-one
  参考文献：
  名称：

  Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals

  摘要：

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.

  DOI：

  10.1021/jo00012a009

文献信息

• Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals
  作者：Derrick L. J. Clive、Sylvain Daigneault

  DOI：10.1021/jo00012a009

  日期：1991.6

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.