(1S)-10-chlorocamphor

• 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-chlorocamphor
• 英文别名: (1S)-10-Chlorcampher；(1S,4R)-1-(chloromethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one；10-chlorocamphor；(1S)-10-chloro-bornan-2-one；(1S)-10-Chlor-bornan-2-on；(1S,4R)-1-(Chloromethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: PKTBHNPYHOMBAI-GMSGAONNSA-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：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-10-chlorocamphor 在 二氯化二硫 、 tetraphosphorus decasulfide 、 间氯过氧苯甲酸 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  三环四硫氨酸和五硫平的合成与反应：α-二硫键的新形成

  摘要：

  通过两种方法合成了含有降冰片烷骨架的环多硫烷（四硫嘧啶和五硫平）。一种是樟脑用二氯化二硫硫化，另一种是硫樟油与二氯化二硫的反应。用LiEt 3 BH还原四硫霉素得到相应的二硫醇，该二硫醇进一步与甲基碘反应，得到相应的甲基硫醚。四硫磷与（Ph 3 P）2 PdCl 2或NiBr 2的反应导致形成相应的二硫代金属配合物。Tetrathiins被立体选择性地通过氧化米-CPBA，得到相应的α-disulfines。

  DOI：

  10.1016/j.tet.2012.05.069
• 作为产物：
  描述：

  右旋樟脑-10-磺酰氯 在 三乙胺盐酸盐 、 copper dichloride 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到(1S)-10-chlorocamphor
  参考文献：
  名称：

  Unexpected formation of 10-iodo- and 10-chlorocamphor under halosulfonylation conditions, and convenient routes to 10-chloro- and 10-bromocamphor

  摘要：

  The generation of camphor-10-sulfonyl iodide in situ under halosulfonylation conditions or exposure of camphor-10-sulfonyl chloride to copper(II) chloride under Asscher-Vofsi conditions leads unexpectedly to the formation of 10-iodocamphor or 10-chlorocamphor, respectively. Additionally, convenient syntheses of 10-bromocamphor and 10-chlorocamphor have been achieved by extension of a previously reported methodology. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.012

文献信息

• Synthesis of (1R)-[1-D]-.alpha.-fenchocamphoronequinone
  作者：W. C. M. C. Kokke、Frans A. Varkevisser

  DOI：10.1021/jo00925a011

  日期：1974.6
• 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.
• Unexpected reactivity of 1-amine-2-methylenenorbornane hydrochlorides with m-CPBA
  作者：Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Santiago de la Moya Cerero、Paloma Martínez Ruiz、Cristina Diaz Morillo、Beatriz Lora Maroto

  DOI：10.1016/j.tetlet.2007.06.131

  日期：2007.8

  Two different 1-amino-3,3-dimethyl-2-methylenenorbornane hydrochlorides, a primary ammonium chloride and a tertiary one, react unexpectedly with m-CPBA (meta-chloroperbenzoic acid) according to two different paths. The primary ammonium chloride gives place to a diastereomeric mixture of the corresponding spiranic 1-nitronorbornane-based epoxides, whereas the tertiary derivative undergoes a skeleton rearrangement giving 10-chlorocamphor. The results are interpreted in terms of competitive reaction pathways controlled by the nitrogenated group located at the Cl norbornane position. (c) 2007 Elsevier Ltd. All rights reserved.
• Nishikawa, Proceedings of the Japan Academy, 1953, vol. 29, p. 30
  作者：Nishikawa

  DOI：——

  日期：——
• Nishikawa; Hagiwara, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 76,79
  作者：Nishikawa、Hagiwara

  DOI：——

  日期：——