(+/-)-3.3-dimethyl-1-bromomethyl-norbornanone-(2) | 99304-44-6

• 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: (+/-)-3.3-dimethyl-1-bromomethyl-norbornanone-(2)
• 英文别名: (+/-)-3.3-Dimethyl-1-brommethyl-norbornanon-(2)；(1S,4S)-1-(bromomethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 99304-44-6
• 化学式: C₁₀H₁₅BrO
• 分子量: 231.132
• InChiKey: VNICVSXTJSSULW-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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,4S)-2,7,7-trimethyl-1-bicyclo[2.2.1]hept-2-enyl] trifluoromethanesulfonate 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 三氟甲磺酸 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 (+/-)-3.3-dimethyl-1-bromomethyl-norbornanone-(2)
  参考文献：
  名称：

  First efficient preparation of enantiopure 10-bromofenchone: the key intermediate to C10-substituted fenchone-derived chiral sources

  摘要：

  DOI：

  10.1016/s0040-4039(01)01316-8

文献信息

• The Rearrangement of Bromofenchone by Base. The Structure of γ-Fencholenic Acid and the Synthesis of Dihydro-α-fencholenic Acid
  作者：D. S. Tarbell、F. C. Loveless

  DOI：10.1021/ja01541a046

  日期：1958.4
• 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.
• First efficient preparation of enantiopure 10-bromofenchone: the key intermediate to C10-substituted fenchone-derived chiral sources
  作者：Antonio Garcı́a Martı́nez、Enrique Teso Vilar、Amelia Garcı́a Fraile、Santiago de la Moya Cerero、Beatriz Lora Maroto

  DOI：10.1016/s0040-4039(01)01316-8

  日期：2001.9