(1R*,5R*,6R*)-1-(Hydroxymethyl)-6-<(2S*,3S*)-3-methyloxiran-2-yl>-2-oxobicyclo<3.1.0>hexane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,5R*,6R*)-1-(Hydroxymethyl)-6-<(2S*,3S*)-3-methyloxiran-2-yl>-2-oxobicyclo<3.1.0>hexane
• 英文别名: (1R*,5R*,6R*)-1-(Hydroxymethyl)-6-((2S*,3S*)-3-methyloxiran-2-yl)-2-oxobicyclo[3.1.0]hexane；(1R,5R,6R)-1-(hydroxymethyl)-6-[(2S,3S)-3-methyloxiran-2-yl]bicyclo[3.1.0]hexan-2-one
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: GXKBMIFTGNDAKY-STCDKJGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R*,5R*,6R*)-1-(Hydroxymethyl)-6-<(2S*,3S*)-3-methyloxiran-2-yl>-2-oxobicyclo<3.1.0>hexane 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以100%的产率得到(3R*,3aR*,3bR*,6aR*)-3,3a,3b,4,5,6-Hexahydro-3-<(1S*)-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
• 作为产物：
  描述：

  sorbyl bromide 在 3 A molecular sieve 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 、 甲苯 为溶剂， 反应 4.05h， 生成 (1R*,5R*,6R*)-1-(Hydroxymethyl)-6-<(2S*,3S*)-3-methyloxiran-2-yl>-2-oxobicyclo<3.1.0>hexane
  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.