exo-3-acetoxytricyclo[5.2.1.0^2,6]deca-4,8-dien | 203715-78-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: exo-3-acetoxytricyclo[5.2.1.0^2,6]deca-4,8-dien
• 英文别名: [(1R,2S,3S,6R,7S)-3-tricyclo[5.2.1.02,6]deca-4,8-dienyl] acetate
• CAS: 203715-78-0
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QXRPTBFQCMXUIE-LVEVGFFFSA-N

物化性质

• 沸点：
  263.4±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-3-acetoxytricyclo[5.2.1.0^2,6]deca-4,8-dien 、 N-甲基对甲苯磺酰胺 在 copper(II) bis(trifluoromethanesulfonate) t-BuOOAc 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以89%的产率得到N,4-dimethyl-N-[(1R,2S,3S,6R,7S)-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides

  摘要：

  A copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates has been developed which is suitable for the coupling of a wide variety of functionalized sulfonamide nucleophiles with acetate electrophiles. The methodology allows for the amidation of benzylic substrates which are not further activated by an additional adjacent alkene or alkyne, enabling simple allylic acetates and primary benzylic acetates to be used as reaction partners. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.135
• 作为产物：
  描述：

  (3aR)-3aα,4,7,7aα-tetrahydro-4α,7α-methano-1(H)-inden-1α-ol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以45%的产率得到exo-3-acetoxytricyclo[5.2.1.0^2,6]deca-4,8-dien
  参考文献：
  名称：

  Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides

  摘要：

  A copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates has been developed which is suitable for the coupling of a wide variety of functionalized sulfonamide nucleophiles with acetate electrophiles. The methodology allows for the amidation of benzylic substrates which are not further activated by an additional adjacent alkene or alkyne, enabling simple allylic acetates and primary benzylic acetates to be used as reaction partners. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.135

文献信息

• Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides
  作者：David A. Powell、Guillaume Pelletier

  DOI：10.1016/j.tetlet.2008.02.135

  日期：2008.4

  A copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates has been developed which is suitable for the coupling of a wide variety of functionalized sulfonamide nucleophiles with acetate electrophiles. The methodology allows for the amidation of benzylic substrates which are not further activated by an additional adjacent alkene or alkyne, enabling simple allylic acetates and primary benzylic acetates to be used as reaction partners. (c) 2008 Elsevier Ltd. All rights reserved.