(1R)-3-endo-(bromomethyl)-3-methyl-2-methylenenorborn-1-yl triflate | 667464-56-4

• 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)-3-endo-(bromomethyl)-3-methyl-2-methylenenorborn-1-yl triflate
• 英文别名: [(1R,3R,4R)-3-(bromomethyl)-3-methyl-2-methylidene-1-bicyclo[2.2.1]heptanyl] trifluoromethanesulfonate
• CAS: 667464-56-4
• 化学式: C₁₁H₁₄BrF₃O₃S
• 分子量: 363.196
• InChiKey: KRGOSKDLCIJIEU-KXUCPTDWSA-N

物化性质

• 沸点：
  328.9±42.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-3-endo-(bromomethyl)-3-methyl-2-methylenenorborn-1-yl triflate 在 lithium aluminium tetrahydride 作用下， 反应 24.0h， 以93%的产率得到(1R)-3-endo-(bromomethyl)-3-methyl-2-methylenenorbornan-1-ol
  参考文献：
  名称：

  Enantiospecific Access to Various C(9),C(10)-Disubstituted Camphors:  Scope and Limitations

  摘要：

  The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-S-, or Se-substituted camphors.

  DOI：

  10.1021/jo049462b
• 作为产物：
  描述：

  (+)-3,9-dibromocamphor 在 triisobutylamine 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1R)-3-endo-(bromomethyl)-3-methyl-2-methylenenorborn-1-yl triflate
  参考文献：
  名称：

  螺环氧化1-降冰片基三氟甲磺酸酯溶剂解中的立体电子控制：3-溴甲基衍生物中的意外反应

  摘要：

  有趣的降冰片烷稠合的四氢呋喃，在降冰片烷骨架中具有额外的合成上有价值的邻二氧基取代，是从对映体樟脑衍生的3-内-溴甲基取代的螺环环氧-1-降冰片基三氟甲磺酸酯高对映体获得的。该过程通过由溴原子立体电子控制的多米诺反应进行。所描述的方法具有合成价值，因为它为将来从樟脑制备对映体特异性的2,3-二取代的四氢呋喃开辟了道路。

  DOI：

  10.1016/j.tetlet.2011.02.006

文献信息

• Martinez, Antonio Garcia; Vilar, Enrique Teso; Fraile, Amelia Garcia, Synlett, 2004, # 1, p. 134 - 136
  作者：Martinez, Antonio Garcia、Vilar, Enrique Teso、Fraile, Amelia Garcia、Cerero, Santiago Moya de la、Morillo, Cristina Diaz、Morillo, Rocio Perez

  DOI：——

  日期：——
• Enantiospecific Access to Various C(9),C(10)-Disubstituted Camphors:  Scope and Limitations
  作者：Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Santiago de la Moya Cerero、Cristina Díaz Morillo、Rocío Pérez Morillo

  DOI：10.1021/jo049462b

  日期：2004.10.1

  The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-S-, or Se-substituted camphors.
• Stereoelectronic control in the solvolysis of spiroepoxidic 1-norbornyl triflates: unexpected reactivity in 3-bromomethyl derivatives
  作者：Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Santiago de la Moya Cerero、Cristina Díaz Morillo

  DOI：10.1016/j.tetlet.2011.02.006

  日期：2011.4

  are enantiospecifically obtained in high yield from epimeric camphor-derived 3-endo-bromomethyl-substituted spiroepoxidic 1-norbornyl triflates. The process takes place via a domino reaction stereoelectronically controlled by the bromine atom. The described process has synthetic value, since it opens the way for a future enantiospecific preparation of 2,3-disubstituted tetrahydrofurans from camphor

  有趣的降冰片烷稠合的四氢呋喃，在降冰片烷骨架中具有额外的合成上有价值的邻二氧基取代，是从对映体樟脑衍生的3-内-溴甲基取代的螺环环氧-1-降冰片基三氟甲磺酸酯高对映体获得的。该过程通过由溴原子立体电子控制的多米诺反应进行。所描述的方法具有合成价值，因为它为将来从樟脑制备对映体特异性的2,3-二取代的四氢呋喃开辟了道路。