bicyclo<2.2.2>oct-2-ene-trans-2,3-dicarboxylic acid | 28871-80-9

• 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: bicyclo<2.2.2>oct-2-ene-trans-2,3-dicarboxylic acid
• 英文别名: bicyclo<2.2.2>oct-5-ene-trans-2,3-dicarboxylic acid；bicyclo<2.2.2>oct-5-ene 2,3-endo,exo-dicarboxylic acid；bicyclo<2.2.2>oct-5-ee-trans-2,3-dicarboxylic acid；trans-Bicyclo<2.2.2>oct-2-en-5,6-dicarbonsaeure；(+/-)-bicyclo[2.2.2]oct-5-ene-2endo,3exo-dicarboxylic acid；(+/-)-Bicyclo[2.2.2]octen-(5)-dicarbonsaeure-(2endo.3exo)；(+/-)-Bicyclo[2.2.2]oct-5-en-2endo,3exo-dicarbonsaeure；(1R,2R,3R,4S)-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid
• CAS: 28871-80-9
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: FUBZERMWPMTSEB-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2917209090

反应信息

• 作为反应物：
  描述：

  bicyclo<2.2.2>oct-2-ene-trans-2,3-dicarboxylic acid 在 sodium azide 、 碘 、 碳酸氢钠 、 potassium iodide 作用下， 以 乙醇 、 水 为溶剂， 生成 exo-2-ethoxycarbonylamino-4-oxo-5-oxa-exo-10-iodotricyclo<4.3.1.0^3,7>decane
  参考文献：
  名称：

  Inokuma, Shun; Sugie, Akihiko; Moriguchi, Koichi, Heterocycles, 1982, vol. 19, # 8, p. 1419 - 1426

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-Bicyclo[2.2.2]octen-(5)-2,3-dicarboxychlorid 在 水 作用下， 生成 bicyclo<2.2.2>oct-2-ene-trans-2,3-dicarboxylic acid
  参考文献：
  名称：

  Gastel, F. J. C. van; Klunder, A. J. H.; Zwanenburg, B., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 175 - 184

  摘要：

  DOI：

文献信息

• Simple and highly efficient chiral dopant molecules possessing both rod- and arch-like units
  作者：Keiki Kishikawa、Shota Aoyagi、Michinari Kohri、Tatsuo Taniguchi、Masahiro Takahashi、Shigeo Kohmoto

  DOI：10.1039/c4sm01214c

  日期：——

  A simple chiral dopant molecule, (R)-1, possessing both rod- and arch-like units was prepared. It showed extremely large helical twisting powers (+123 to +228 μm⁻¹) with P-helicity in nematic liquid crystal phases.

  一个简单的手性掺杂分子，（R）-1，具有棒状和拱形单元。它在向列型液晶相中表现出极大的螺旋扭转功率（+123至+228 μm⁻¹），具有P螺旋度。
• OXYMERCURATION OF Δ⁵-[2,2,2]-BICYCLOÖCTENE
  作者：D. D. K. Chiu、George F Wright

  DOI：10.1139/v59-209

  日期：1959.9.1

  It has now been shown that an earlier assignment of configuration in which 1,4-↑↑-ethylene-Δ⁵-cyclohexenedicarboxylic acids and their derivatives were presumed to form with mercuric salts 5-↓-hydroxy-6-↓-anionomercuri-1,4-↑↑-ethylenecyclohexanedicarboxylic acid derivatives is incorrect. Instead 5-↓-hydroxy-6-↑-anionomercuri-1,4-↑↑-ethylenecyclohexanedicarboxylic acid derivatives are formed, similarly with the homologous 5-↓-hydroxy-6-↑-anionomercuri-1,4-methylenecyclohexane-2,3-dicarboxylic acid derivatives. This similarity is exemplified by comparable dipole moments. The exception is 5-↓-hydroxy-6-↓-chloromercuri-1,4-↑↑-methylenecyclohexane-2,3-↓↓-dicarboxylic acid, γ-lactone, which has a configuration opposite to all of the others of these series having boat-type cyclohexane ring conformations. The exception is attributed to steric effects.

  现在已经显示，先前假定1,4-↑↑-乙烯-Δ⁵-环己烯二羧酸及其衍生物与汞盐形成5-↓-羟基-6-↓-阴离子汞基-1,4-↑↑-乙烯环己二羧酸衍生物的构型是错误的。相反，形成了5-↓-羟基-6-↑-阴离子汞基-1,4-↑↑-乙烯环己二羧酸衍生物，类似于同系物5-↓-羟基-6-↑-阴离子汞基-1,4-亚甲基环己烷-2,3-二羧酸衍生物。这种相似性通过可比的偶极矩来加以说明。例外是5-↓-羟基-6-↓-氯汞基-1,4-↑↑-亚甲基环己烷-2,3-↓↓-二羧酸，γ-内酯，其构型与这个系列中所有其他具有船型环己烷环构象的物质相反。这个例外归因于立体效应。
• The role of the CC double bond in alcohol elimination from MH+ ions of unsaturated bicyclic esters upon chemical ionization
  作者：N. Khaselev、A. Mandelbaum

  DOI：10.1002/jms.1190301103

  日期：1995.11

  Methyl and ethyl endo- and exo-bicyclo [2.2.2] oct-5-ene-2-carboxylates exhibit different mass spectral behaviour under i-Bu-chemical ionization (CI) conditions and upon collision-induced dissociation (CID) of their MH+ IONS. The endo-esters exhibit m/z 135 [MH  MeOH]+ and [MH  EtOH]+ ions, which are absent in the i-Bu-CI mass spectra of the exo-isomers. This stereospecific behavior is explained in terms of the proton bridging requirement in the alcohol elimination from MH+ ions of esters. Such proton bridging between the alkoxycarbonyl group and the double bond is possible in the endo-esters, but not in the exo-isomers. Hydrogen-deuterium exchange processes, observed in the CID spectra of the MD+ ion of the endo-esters, support the proposed mechanistic pathway. Hydrogen bridging with the double bond also plays a role in the alcohol elimination processes of stereoisomeric bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylates.

  甲基和乙基内型和外型双环[2.2.2]辛-5-烯-2-羧酸酯在 i-Bu 化学电离 (CI) 条件下及其碰撞诱导解离 (CID) 下表现出不同的质谱行为MH+ 离子。内酯显示 m/z 135 [MH → MeOH]+ 和 [MH → EtOH]+ 离子，这些离子在外型异构体的 i-Bu-Cl 质谱中不存在。这种立体定向行为可以用从酯的 MH+ 离子消除醇时的质子桥接要求来解释。烷氧基羰基和双键之间的这种质子桥联在内酯中是可能的，但在外异构体中则不然。在内酯 MD+ 离子的 CID 光谱中观察到的氢-氘交换过程支持了所提出的机制途径。双键的氢桥也在立体异构双环[2.2.2]辛-5-烯-2,3-二羧酸酯的醇消除过程中发挥作用。
• Synthesis of exo-bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic anhydrides by thermal isomerization of trans-diacids
  作者：Adrian Weisz、Asher Mandelbaum

  DOI：10.1021/jo00260a003

  日期：1988.12
• Conformational Effects and Hydrogen Bonding in 1,4-Diols
  作者：Lester P. Kuhn、Paul. Von R. Schleyer、William F. Baitinger、Lennart. Eberson

  DOI：10.1021/ja01058a022

  日期：1964.2