(1S)-10-chlorofenchone | 502688-42-8

• 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)-10-chlorofenchone
• 英文别名: 10-Chlorofenchone；(1S*,4S*)-1-Chloromethyl-3,3-dimethyl-bicyclo[2.2.1]heptan-2-one；(1S,4S)-1-(chloromethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 502688-42-8
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: LJKFNCBLXRCFBS-OIBJUYFYSA-N

物化性质

• 沸点：
  252.2±13.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S)-7,7-dimethyl-2-methylenenorbornan-1-ol 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以87%的产率得到(1S)-10-chlorofenchone
  参考文献：
  名称：

  C(10)-Substituted Camphors and Fenchones by Electrophilic Treatment of 2-Methylenenorbornan-1-ols:  Enantiospecificity, Scope, and Limitations

  摘要：

  Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchone-derived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein rearrangement. A complete study of the enantiospecificity, scope, and limitations of this process, as well as about the role played by the hydroxyl group attached at the C(1) bridgehead position of the starting 2-methylenenorbornan-1-ols, has been realized. The feasibility of the described methodology has been exemplified by the highly efficient enantiospecific preparation of several interesting C(10)-halogen-, (C10)-O-, C(10)-S-, C(10)-Se-, or C(10)-C-substituted camphors and fenchones.

  DOI：

  10.1021/jo026566i

文献信息

• Multinuclear NMR study of 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one (fenchone) and its six monochlorinated derivatives
  作者：E. Kolehmainen、K. Laihia、J. Korvola、R. Kauppinen、M. Pitkänen、B. Mannila、E. Mannila

  DOI：10.1002/mrc.1260280914

  日期：1990.9

  1H, 13C and 17O NMR spectra of fenchone and six monochlorofenchones have been recorded. The second‐order 1H NMR spectra were analysed by an iterative computer program. The 1H and 13C chlorine‐induced substituent chemical shifts (SCS) were calculated. The vicinal coupling constants proved to be essential in the assignment of the chemical shifts of the geminal methyls. No clear correlation was observed

  已经记录了茴香酮和六种一氯茴香酮的 1H、13C 和 17O NMR 光谱。二阶 1H NMR 谱通过迭代计算机程序进行分析。计算了 1H 和 13C 氯诱导的取代基化学位移（SCS）。邻位偶联常数被证明在指定孪生甲基的化学位移中是必不可少的。在羰基氧和羰基碳的化学位移之间没有观察到明显的相关性。所有的一氯芬酮都是以前未知的化合物，是为这项工作合成的。
• C(10)-Substituted Camphors and Fenchones by Electrophilic Treatment of 2-Methylenenorbornan-1-ols:  Enantiospecificity, Scope, and Limitations
  作者：Santiago de la Moya Cerero、Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Beatriz Lora Maroto

  DOI：10.1021/jo026566i

  日期：2003.2.1

  Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchone-derived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein rearrangement. A complete study of the enantiospecificity, scope, and limitations of this process, as well as about the role played by the hydroxyl group attached at the C(1) bridgehead position of the starting 2-methylenenorbornan-1-ols, has been realized. The feasibility of the described methodology has been exemplified by the highly efficient enantiospecific preparation of several interesting C(10)-halogen-, (C10)-O-, C(10)-S-, C(10)-Se-, or C(10)-C-substituted camphors and fenchones.