(-)-(1R,4R)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)methanol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(1R,4R)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)methanol
• 英文别名: [(1R,4R)-7,7-dimethyl-2-methylidene-1-bicyclo[2.2.1]heptanyl]methanol
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: XSXPGKDUWFRNSR-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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

• 作为产物：
  描述：

  methylenedimethyl sulfurane 、 (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 (+)-fenchone 、 盐酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 氯仿 为溶剂， 反应 22.0h， 生成 [(1S,4S)-2,7,7-trimethyl-1-bicyclo[2.2.1]hept-2-enyl]methanol 、 (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)methanol 、 (-)-(1R,4R)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)methanol
  参考文献：
  名称：

  First synthesis of (−)-(1R,4R)- and (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)-methanol: new fenchone-derived chiral auxiliaries

  摘要：

  The treatment of (+)- or (-)-fenchones epoxides with 1:2 85% H3PO4:DMSO for 30 min at 20 degreesC induced an enantiospecific Wagner-Meerwein rearrangement affording new C(10)-O-substituted camphor derivatives which could prove useful as chiral auxiliaries. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00403-7

文献信息

• First synthesis of (−)-(1R,4R)- and (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)-methanol: new fenchone-derived chiral auxiliaries
  作者：Pascal Gosselin、Martine Lelièvre、Bénédicte Poissonnier

  DOI：10.1016/s0957-4166(01)00403-7

  日期：2001.8

  The treatment of (+)- or (-)-fenchones epoxides with 1:2 85% H3PO4:DMSO for 30 min at 20 degreesC induced an enantiospecific Wagner-Meerwein rearrangement affording new C(10)-O-substituted camphor derivatives which could prove useful as chiral auxiliaries. (C) 2001 Elsevier Science Ltd. All rights reserved.