(1S)-9-bromo-10-[(p-nitrophenyl)sulfanyl]camphor

• 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: (1S)-9-bromo-10-[(p-nitrophenyl)sulfanyl]camphor
• 英文别名: (1S,4R,7R)-7-(bromomethyl)-7-methyl-1-[(4-nitrophenyl)sulfanylmethyl]bicyclo[2.2.1]heptan-2-one
• 化学式: C₁₆H₁₈BrNO₃S
• 分子量: 384.294
• InChiKey: QADNDVTXOBCNII-HFBAOOFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+)-3,9-dibromocamphor 在 lithium aluminium tetrahydride 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1S)-9-bromo-10-[(p-nitrophenyl)sulfanyl]camphor
  参考文献：
  名称：

  Enantiospecific Access to Various C(9),C(10)-Disubstituted Camphors:  Scope and Limitations

  摘要：

  The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-S-, or Se-substituted camphors.

  DOI：

  10.1021/jo049462b

文献信息

• Enantiospecific Access to Various C(9),C(10)-Disubstituted Camphors:  Scope and Limitations
  作者：Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Santiago de la Moya Cerero、Cristina Díaz Morillo、Rocío Pérez Morillo

  DOI：10.1021/jo049462b

  日期：2004.10.1

  The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-S-, or Se-substituted camphors.