(1R,4R)-(+)-1-bromomethyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane | 341511-69-1

• 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)-(+)-1-bromomethyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane
• 英文别名: (1R,4R)-1-(bromomethyl)-3,3-dimethyl-2-methylidenebicyclo[2.2.1]heptane
• CAS: 341511-69-1
• 化学式: C₁₁H₁₇Br
• 分子量: 229.16
• InChiKey: LSTRYCAWGYICKA-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1R,4R)-(+)-1-bromomethyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (1S,4R)-(+)-1-methyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane
  参考文献：
  名称：

  Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

  摘要：

  Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00089-2
• 作为产物：
  描述：

  (1S,4R)-1,7,7-Trimethyl-2-methylene-bicyclo[2.2.1]heptane 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(1R,4R)-(+)-1-bromomethyl-3,3-dimethyl-2-methylenebicyclo[2.2.1]heptane
  参考文献：
  名称：

  Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

  摘要：

  Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00089-2

文献信息

• Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system
  作者：Allen A Thomas、Keith A Monk、Sonia Abraham、Stella Lee、Charles M Garner

  DOI：10.1016/s0040-4039(01)00089-2

  日期：2001.3

  Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure. (C) 2001 Elsevier Science Ltd. All rights reserved.