1-chloromethylbicyclo<2,2,1>heptane

• 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: 1-chloromethylbicyclo<2,2,1>heptane
• 英文别名: 1-norbornylmethyl chloride；1-(Chloromethyl)norbornane；1-(chloromethyl)bicyclo[2.2.1]heptane
• 化学式: C₈H₁₃Cl
• mdl: MFCD19233110
• 分子量: 144.644
• InChiKey: BPSUCXCLRMYWCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(羟甲基)双环(2.2.1)庚烷 在 吡啶 、 氯化亚砜 作用下， 反应 0.5h， 生成 1-chloromethylbicyclo<2,2,1>heptane
  参考文献：
  名称：

  The Carbene Fragmentation−Ring Expansion Route to Bridgehead Carbocations

  摘要：

  [GRAPHICS]The products, kinetics, and activation parameters were determined for the fragmentation-ring expansions of 1-norbornylmethyloxychlorocarbene (11) and 3-noradamantylmethyloxychlorocarbene (17). Products from 11 (in dichloroethane) included 1-chlorobicyclo[2.2.2]octane (9, 56%) and 1-chlorobicyclo[3.2.1]octane (10, 37%); from 17, we obtained I-chloroadamantane (15, 68%) and protoadamantyl chloride (16, 28%).

  DOI：

  10.1021/ol020083j

文献信息

• Fragmentation of alkoxychlorocarbenes in the gas phase
  作者：Michael E Blake、Maitland Jones、Fengmei Zheng、Robert A Moss

  DOI：10.1016/s0040-4039(02)00438-0

  日期：2002.4

  In contrast to photolysis or thermal decomposition in solution, which is dominated by ionic reactions, flash vacuum pyrolysis of alkylchlorodiazirines in the gas phase generates radicals. The cyclopropylcarbinyl system is re-examined and the 1-norbornylcarbinyl system is studied for the first time.

  与以离子反应为主的溶液中的光解或热分解相反，烷基氯二嗪在气相中的快速真空热解会产生自由基。重新检查了环丙基羰基系统，并首次研究了1-降冰片基羰基系统。
• Denney, Donald B.; Garth, Bruce H.; Hanifin, J. William Jr., Phosphorus and Sulfur and the Related Elements, 1980, vol. 8, p. 275 - 280
  作者：Denney, Donald B.、Garth, Bruce H.、Hanifin, J. William Jr.、Relles, Howars M.

  DOI：——

  日期：——
• DENNEY D. B.; GARTH B. H.; HANIFIN J. W.; RELLES H. M., PHOSPH. AND SULFUR, 1980, 8, NO 3, 275-280
  作者：DENNEY D. B.、 GARTH B. H.、 HANIFIN J. W.、 RELLES H. M.

  DOI：——

  日期：——
• The Carbene Fragmentation−Ring Expansion Route to Bridgehead Carbocations
  作者：Robert A. Moss、Fengmei Zheng、Jean-Marie Fedé、Ronald R. Sauers

  DOI：10.1021/ol020083j

  日期：2002.7.1

  [GRAPHICS]The products, kinetics, and activation parameters were determined for the fragmentation-ring expansions of 1-norbornylmethyloxychlorocarbene (11) and 3-noradamantylmethyloxychlorocarbene (17). Products from 11 (in dichloroethane) included 1-chlorobicyclo[2.2.2]octane (9, 56%) and 1-chlorobicyclo[3.2.1]octane (10, 37%); from 17, we obtained I-chloroadamantane (15, 68%) and protoadamantyl chloride (16, 28%).