1-Vinylspiro[3.5]nonan-1-ol | 152568-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Vinylspiro[3.5]nonan-1-ol
• 英文别名: 3-ethenylspiro[3.5]nonan-3-ol
• CAS: 152568-20-2
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: UQTQXSXFKBSDJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Vinylspiro[3.5]nonan-1-ol 在 copper diacetate 、 Mn(pic)3 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以14%的产率得到螺[5.5]-3-十一酮
  参考文献：
  名称：

  Manganese(III)-based oxidative fragmentation-cyclization reactions of unsaturated cyclobutanols

  摘要：

  Allylic cyclobutanols 1, 10, 21, 27, 32, 39, 51, and 58 are oxidatively fragmented by Mn(OAc)3.2H2O in EtOH to give tertiary radicals as shown in eq 1. These tertiary radicals undergo both 6-endocyclization to the alpha,beta--unsaturated ketone to afford a-keto radicals and 5-exo-cyclization to provide beta-keto cyclopentylmethyl radicals. The a-keto radicals produced by 6-endo-cyclization are reduced to ketones or dimerize. The beta-keto radicals formed by 5-exo-cyclization are oxidized by Cu(OAc)2 to yield methylenecyclopentanones and rearrange to give 3-oxocyclohexyl radicals that are oxidized by Cu(OAC)2 to afford cyclohexenones. Acetylenic cyclobutanols 47, 49, and 65 are oxidatively fragmented by Mn(OAC)3.2H2O in EtOH to provide tertiary radicals that cyclize to give alpha-keto vinyl radicals, which abstract a hydrogen atom to yield methylenecyclopentanones. Pentenylcyclobutanol 75 is oxidatively fragmented by Mn(OAc)3.2H2O to afford tertiary radical 74, which cyclizes to furnish cyclopentylmethyl radicals 77 and 78, which are oxidized by Cu(OAC)2 to methylenecyclopentanes 76 and 79.

  DOI：

  10.1021/jo00077a054
• 作为产物：
  描述：

  螺[3.5]壬烷-3-酮 、 乙烯基-锂 以 四氢呋喃 为溶剂， 反应 0.25h， 以88%的产率得到1-Vinylspiro[3.5]nonan-1-ol
  参考文献：
  名称：

  Manganese(III)-based oxidative fragmentation-cyclization reactions of unsaturated cyclobutanols

  摘要：

  Allylic cyclobutanols 1, 10, 21, 27, 32, 39, 51, and 58 are oxidatively fragmented by Mn(OAc)3.2H2O in EtOH to give tertiary radicals as shown in eq 1. These tertiary radicals undergo both 6-endocyclization to the alpha,beta--unsaturated ketone to afford a-keto radicals and 5-exo-cyclization to provide beta-keto cyclopentylmethyl radicals. The a-keto radicals produced by 6-endo-cyclization are reduced to ketones or dimerize. The beta-keto radicals formed by 5-exo-cyclization are oxidized by Cu(OAc)2 to yield methylenecyclopentanones and rearrange to give 3-oxocyclohexyl radicals that are oxidized by Cu(OAC)2 to afford cyclohexenones. Acetylenic cyclobutanols 47, 49, and 65 are oxidatively fragmented by Mn(OAC)3.2H2O in EtOH to provide tertiary radicals that cyclize to give alpha-keto vinyl radicals, which abstract a hydrogen atom to yield methylenecyclopentanones. Pentenylcyclobutanol 75 is oxidatively fragmented by Mn(OAc)3.2H2O to afford tertiary radical 74, which cyclizes to furnish cyclopentylmethyl radicals 77 and 78, which are oxidized by Cu(OAC)2 to methylenecyclopentanes 76 and 79.

  DOI：

  10.1021/jo00077a054

文献信息

• Manganese(III)-based oxidative fragmentation-cyclization reactions of unsaturated cyclobutanols
  作者：Barry B. Snider、Nha Huu Vo、Bruce M. Foxman

  DOI：10.1021/jo00077a054

  日期：1993.12

  Allylic cyclobutanols 1, 10, 21, 27, 32, 39, 51, and 58 are oxidatively fragmented by Mn(OAc)3.2H2O in EtOH to give tertiary radicals as shown in eq 1. These tertiary radicals undergo both 6-endocyclization to the alpha,beta--unsaturated ketone to afford a-keto radicals and 5-exo-cyclization to provide beta-keto cyclopentylmethyl radicals. The a-keto radicals produced by 6-endo-cyclization are reduced to ketones or dimerize. The beta-keto radicals formed by 5-exo-cyclization are oxidized by Cu(OAc)2 to yield methylenecyclopentanones and rearrange to give 3-oxocyclohexyl radicals that are oxidized by Cu(OAC)2 to afford cyclohexenones. Acetylenic cyclobutanols 47, 49, and 65 are oxidatively fragmented by Mn(OAC)3.2H2O in EtOH to provide tertiary radicals that cyclize to give alpha-keto vinyl radicals, which abstract a hydrogen atom to yield methylenecyclopentanones. Pentenylcyclobutanol 75 is oxidatively fragmented by Mn(OAc)3.2H2O to afford tertiary radical 74, which cyclizes to furnish cyclopentylmethyl radicals 77 and 78, which are oxidized by Cu(OAC)2 to methylenecyclopentanes 76 and 79.