(3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1R*)-1-hydroxyethyl>-6-oxo-1H-cyclopenta<1,3>cyclopropa<1,2-c>furan

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1R*)-1-hydroxyethyl>-6-oxo-1H-cyclopenta<1,3>cyclopropa<1,2-c>furan
• 英文别名: (3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-((1R*)-1-hydroxyethyl)-6-oxo-1H-cyclopenta[1,3]cyclopropa[1,2-c]furan；(1R,4S,5R,6R)-4-[(1R)-1-hydroxyethyl]-3-oxatricyclo[4.3.0.01,5]nonan-9-one
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: MENIKFIQUBOSRP-NLULIJGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1R*)-1-hydroxyethyl>-6-oxo-1H-cyclopenta<1,3>cyclopropa<1,2-c>furan 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到(3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1R*)-1-benzoxyethyl>-6-oxo-1H-cyclopenta<1,3>cyclopropa<1,2-c>furan
  参考文献：
  名称：

  Tandem Fragmentation of Cyclopropylcarbinyl/Oxiranylcarbinyl Radicals. On the Reversibility of Oxiranylcarbinyl/Allyloxyl Radical Formation

  摘要：

  The tandem radical fragmentation of four stereoisomeric epoxy thiocarbonates 7c-10c has been investigated. In each instance a cyclopropylcarbinyl radical fragments to generate an oxiranylcarbinyl radical, which, in turn, undergoes fragmentation. The Initially detected product is (Z)-allylic alcohol 23, which isomerizes to (E)-allylic alcohol 24 under acid catalysis. The reversibility of allyloxyl radical formation is considered.

  DOI：

  10.1021/jo00089a012
• 作为产物：
  描述：

  sorbyl bromide 在 3 A molecular sieve 、 三氟乙酸 甲醇 、 copper acetylacetonate 、 disodium hydrogenphosphate 、 正丁基锂 、 对甲苯磺酰叠氮 、 过氧化脲素 、 二异丁基氢化铝 、 二异丙胺 、 三氟乙酸酐 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.05h， 生成 (3S*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1R*)-1-hydroxyethyl>-6-oxo-1H-cyclopenta<1,3>cyclopropa<1,2-c>furan
  参考文献：
  名称：

  Tandem Fragmentation of Cyclopropylcarbinyl/Oxiranylcarbinyl Radicals. On the Reversibility of Oxiranylcarbinyl/Allyloxyl Radical Formation

  摘要：

  The tandem radical fragmentation of four stereoisomeric epoxy thiocarbonates 7c-10c has been investigated. In each instance a cyclopropylcarbinyl radical fragments to generate an oxiranylcarbinyl radical, which, in turn, undergoes fragmentation. The Initially detected product is (Z)-allylic alcohol 23, which isomerizes to (E)-allylic alcohol 24 under acid catalysis. The reversibility of allyloxyl radical formation is considered.

  DOI：

  10.1021/jo00089a012

文献信息

• Ziegler Frederick E., Petersen Anders K., J. Org. Chem, 59 (1994) N 10, S 2707-2714
  作者：Ziegler Frederick E., Petersen Anders K.

  DOI：——

  日期：——
• Tandem Fragmentation of Cyclopropylcarbinyl/Oxiranylcarbinyl Radicals. On the Reversibility of Oxiranylcarbinyl/Allyloxyl Radical Formation
  作者：Frederick E. Ziegler、Anders K. Petersen

  DOI：10.1021/jo00089a012

  日期：1994.5

  The tandem radical fragmentation of four stereoisomeric epoxy thiocarbonates 7c-10c has been investigated. In each instance a cyclopropylcarbinyl radical fragments to generate an oxiranylcarbinyl radical, which, in turn, undergoes fragmentation. The Initially detected product is (Z)-allylic alcohol 23, which isomerizes to (E)-allylic alcohol 24 under acid catalysis. The reversibility of allyloxyl radical formation is considered.