((1S,7S)-3-Hydroxymethyl-7-phenyl-cyclohepta-2,5-dienyl)-methanol | 919299-10-8

• 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: ((1S,7S)-3-Hydroxymethyl-7-phenyl-cyclohepta-2,5-dienyl)-methanol
• 英文别名: [(3S,4S)-4-Phenylcyclohepta-1,5-diene-1,3-diyl]dimethanol；[(1S,7S)-3-(hydroxymethyl)-7-phenylcyclohepta-2,5-dien-1-yl]methanol
• CAS: 919299-10-8
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: OGAJHUKZWKKYOJ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 ((1S,7S)-3-Hydroxymethyl-7-phenyl-cyclohepta-2,5-dienyl)-methanol 、 ((1S,7S)-3-Hydroxymethyl-7-phenyl-cyclohepta-2,5-dienyl)-methanol
  参考文献：
  名称：

  Vinyldiazolactone as a Vinylcarbene Precursor:  Highly Selective C−H Insertion and Cyclopropanation Reactions

  摘要：

  Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.

  DOI：

  10.1021/ja066452e

文献信息

• Vinyldiazolactone as a Vinylcarbene Precursor:  Highly Selective C−H Insertion and Cyclopropanation Reactions
  作者：Darren Bykowski、Kou-Hui Wu、Michael P. Doyle

  DOI：10.1021/ja066452e

  日期：2006.12.1

  Vinylcarbenes are versatile synthetic intermediates, capable of asymmetric cyclopropanation and insertion into unactivated C-H bonds. The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyldiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions. Dirhodium azetidinone ligated compounds are optimal catalysts. Cyclopropanation coupled with the Cope rearrangement provides access to trans-3,4-disubstituted hydroazulenes.