(1R,4S,7R)-2-Ethyl-7-methoxy-bicyclo[2.2.1]hepta-2,5-diene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,7R)-2-Ethyl-7-methoxy-bicyclo[2.2.1]hepta-2,5-diene
• 英文别名: (1R,4S,7R)-2-ethyl-7-methoxybicyclo[2.2.1]hepta-2,5-diene
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: FSHXTIPRNUAASX-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1R,4S,7R)-2-Ethyl-7-methoxy-bicyclo[2.2.1]hepta-2,5-diene 在 氰基萘 作用下， 以 乙腈 为溶剂， 生成 (1S,2S,3R,4S,6R)-1-Ethyl-3,5-dimethoxy-tricyclo[2.2.1.0^2,6]heptane
  参考文献：
  名称：

  Electron transfer photochemistry of 7-(spirocyclopropane)quadricyclane: capture of a radical cation and sequential cyclopropylcarbinyl rearrangements

  摘要：

  The electron transfer photo-sensitized reaction of 7-(spiroeyclopropane)quadricyclane (1) with methanol produces two rearranged mono-methanol adducts, 2 and 3, and abis-methanol adduct, 4. The products reveal that 1(.+) reacts by stereo-and regiospecific attack of methanol on one trisubstituted cyclopropane ring, The resulting free radical rapidly undergoes one or two (consecutive) cyctopropylcarbinyl to butenyl rearrangements. The mono-adducts are formed by net hydrogen abstraction, the di-adduct via a (secondary) electron transfer reaction of 3. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199708)10:8<607::aid-poc931>3.0.co;2-p
• 作为产物：
  描述：

  甲醇 、 7-(spirocyclopropane)quadicyclane 在 氰基萘 作用下， 以 乙腈 为溶剂， 以30%的产率得到7-methoxy-5-spirocyclopropanebicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Electron transfer photochemistry of 7-(spirocyclopropane)quadricyclane: capture of a radical cation and sequential cyclopropylcarbinyl rearrangements

  摘要：

  The electron transfer photo-sensitized reaction of 7-(spiroeyclopropane)quadricyclane (1) with methanol produces two rearranged mono-methanol adducts, 2 and 3, and abis-methanol adduct, 4. The products reveal that 1(.+) reacts by stereo-and regiospecific attack of methanol on one trisubstituted cyclopropane ring, The resulting free radical rapidly undergoes one or two (consecutive) cyctopropylcarbinyl to butenyl rearrangements. The mono-adducts are formed by net hydrogen abstraction, the di-adduct via a (secondary) electron transfer reaction of 3. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199708)10:8<607::aid-poc931>3.0.co;2-p

文献信息

• Electron transfer photochemistry of 7-(spirocyclopropane)quadricyclane: capture of a radical cation and sequential cyclopropylcarbinyl rearrangements
  作者：Sean McIlroy、Hengxin Weng、Heinz D. Roth

  DOI：10.1002/(sici)1099-1395(199708)10:8<607::aid-poc931>3.0.co;2-p

  日期：1997.8

  The electron transfer photo-sensitized reaction of 7-(spiroeyclopropane)quadricyclane (1) with methanol produces two rearranged mono-methanol adducts, 2 and 3, and abis-methanol adduct, 4. The products reveal that 1(.+) reacts by stereo-and regiospecific attack of methanol on one trisubstituted cyclopropane ring, The resulting free radical rapidly undergoes one or two (consecutive) cyctopropylcarbinyl to butenyl rearrangements. The mono-adducts are formed by net hydrogen abstraction, the di-adduct via a (secondary) electron transfer reaction of 3. (C) 1997 by John Wiley & Sons, Ltd.