(1R,2S,4R,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl benzoate | 1418603-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,4R,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl benzoate
• CAS: 1418603-03-8
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: XGWUOCNZFKMMJP-MPTYRVRUSA-N

物化性质

• 沸点：
  370.3±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-yl benzoate 在 bis(cyclopentadienyl)titanium (III) chloride 、 sodium dihydrogenphosphate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.83h， 以86%的产率得到[(1S,3R,5R)-3-hydroxy-2-methylidene-5-prop-1-en-2-ylcyclohexyl] benzoate
  参考文献：
  名称：

  Titanocene-promoted stereoselective eliminations on epoxy alcohols derived from R-(−)-carvone

  摘要：

  The reaction of several stereoisomeric epoxy alcohols, obtained from R-(-)-carvone, and their corresponding formates, acetates, and benzoates, promoted by Cp2TiCl has been studied. The different outcomes of the reaction of epoxy derivatives are rationalized in terms of mechanistically biased processes. The radicals emerging from oxirane cleavage provide two types of reaction: dehydroxylation (deoxy-carbonylation) and dehydrogenation.The results offer considerable support for the radical elimination theory of hydroxyl, formyloxyl, and acetoxyl groups. The inability of tertiary radicals to be reduced by the Ti(III) complex is demonstrated unequivocally. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.093