1,4,4a,5,8,8a-hexahydro-1,4-exo-oxa-5,8-exo-methanonaphthalene-4a,8a-dicarboxylic anhydride | 81423-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1,4,4a,5,8,8a-hexahydro-1,4-exo-oxa-5,8-exo-methanonaphthalene-4a,8a-dicarboxylic anhydride
• CAS: 81423-99-6
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: GCNABOSHBBSECP-MLIYIKKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4,4a,5,8,8a-hexahydro-1,4-exo-oxa-5,8-exo-methanonaphthalene-4a,8a-dicarboxylic anhydride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,4-exo-oxa-5,8-exo-methanonaphthalene-4a,8a-dicarboxylic anhydride
  参考文献：
  名称：

  Reactivities of norbornene-type double bonds in propellane derivatives and their precursors; furan as a diene

  摘要：

  DOI：

  10.1021/ja00375a032
• 作为产物：
  描述：

  呋喃 、 norbornadiene-2,3-dicarboxylic anhydride 反应 18.0h， 以97%的产率得到1,4,4a,5,8,8a-hexahydro-1,4-exo-oxa-5,8-exo-methanonaphthalene-4a,8a-dicarboxylic anhydride
  参考文献：
  名称：

  Reactivities of norbornene-type double bonds in propellane derivatives and their precursors; furan as a diene

  摘要：

  DOI：

  10.1021/ja00375a032

文献信息

• The preparation of 7-substituted norbornadiene-2,3-dicarboxylic anhydrides and an experimental and theoretical study of their reactivity
  作者：Davor Margetić、Ronald N. Warrener、Guangxing Sun、Douglas N. Butler

  DOI：10.1016/j.tet.2007.03.009

  日期：2007.5

  Four new substituted methano-bridged or heteroatom-bridged norbornadienomaleic anhydrides have been prepared and converted to sesquinorbornadiene anhydrides by reaction with cyclic 1,3-dienes. The versatility of parity reversal, in conjunction with N-substituent steric effects, has been used to produce all three possible stereoisomers of the NO-sesquinorbomadiene anhydrides in separate, stereoselective cycloadditions. The anhydrides have been synthesized by cyclization of their diacids (in situ production) or by flash vacuum pyrolysis of their furan adducts (yielding crystalline products); further fragmentation occurs at these or higher temperatures to produce five-membered carbocyclic or heterocyclic anhydrides. Activation energies have been evaluated for the fragmentation and cycloaddition processes using DFT calculations (B3LYP/6-31G*) and these calculations correctly predict, which reaction can be intercepted at the norbornadienomaleic anhydride stage and preferred stereochemistry of cycloadducts. (C) 2007 Elsevier Ltd. All rights reserved.
• Butler, Douglas N.; Margetic, Davor; O'Neill, Peter J. C., Synlett, 2000, # 1, p. 98 - 100
  作者：Butler, Douglas N.、Margetic, Davor、O'Neill, Peter J. C.、Warrener, Ronald N.

  DOI：——

  日期：——