norbornadiene-2,3-dicarboxylic anhydride | 17397-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: norbornadiene-2,3-dicarboxylic anhydride
• 英文别名: bicyclo[2.2.1]hepta--2,5-diene-2,3-dicarboxylic anhydride；(1R,7S)-4-oxatricyclo[5.2.1.02,6]deca-2(6),8-diene-3,5-dione
• CAS: 17397-31-8
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: DJGDZQOVXNLQQH-SYDPRGILSA-N

物化性质

• 沸点：
  342.8±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  norbornadiene-2,3-dicarboxylic anhydride 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 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：

  2,5-降冰片二烯-2,3-二羧酸 在 乙酸酐 作用下， 反应 2.0h， 生成 norbornadiene-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  具有适应性的pH响应降解性的易于接枝的双环α，β-不饱和酸酐的开环易位聚合

  摘要：

  通过开环复分解聚合（ROMP）合成了具有α，β-不饱和酸酐作为重复单元的聚合物。酸酐部分已准备好与胺接枝，形成酸不稳定的顺式α，β-不饱和酰胺键。可通过改变酸和酰胺基团之间的分子内可及性来控制pH响应的可逆接枝。根据酸酐结构，阿仑膦酸盐接枝的ROMP聚合物表现出不同的pH依赖性细胞毒性。

  DOI：

  10.1002/anie.201806763

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.
• Ring Opening Metathesis Polymerization of Bicyclic α,β-Unsaturated Anhydrides for Ready-to-be-grafted Polymers Having Tailored pH-Responsive Degradability
  作者：Heejin Kim、Sungwhan Kim、Sunyoung Kang、Youngjun Song、Suyong Shin、Seonju Lee、Minji Kang、So Hee Nam、Yan Lee

  DOI：10.1002/anie.201806763

  日期：2018.9.17

  Polymers having α,β‐unsaturated anhydrides as repeating units were synthesized by ring opening metathesis polymerization (ROMP). The anhydride moieties were ready‐to‐be‐grafted with amines to form acid‐labile cis‐α,β‐unsaturated acid amide linkages. The pH‐responsive reversible de‐grafting can be controlled by changing the intramolecular accessibility between acid and amide groups. The alendronate‐grafted

  通过开环复分解聚合（ROMP）合成了具有α，β-不饱和酸酐作为重复单元的聚合物。酸酐部分已准备好与胺接枝，形成酸不稳定的顺式α，β-不饱和酰胺键。可通过改变酸和酰胺基团之间的分子内可及性来控制pH响应的可逆接枝。根据酸酐结构，阿仑膦酸盐接枝的ROMP聚合物表现出不同的pH依赖性细胞毒性。
• Reactivities of norbornene-type double bonds in propellane derivatives and their precursors; furan as a diene
  作者：Paul D. Bartlett、Gerald L. Combs、Ai Xuan Thi Le、William H. Watson、Jean Galloy、Michio Kimura

  DOI：10.1021/ja00375a032

  日期：1982.6