cyclooctatetraene-1,4-dicarboxylic acid | 82878-17-9

• 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: cyclooctatetraene-1,4-dicarboxylic acid
• 英文别名: (1E,2Z,4E,6Z)-cycloocta-2,4,6,8-tetraene-1,4-dicarboxylic acid
• CAS: 82878-17-9
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: IJLJAKXMUBVBRS-OZFFZRAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,4-立方烷二羧酸 以 环丁砜 为溶剂， 反应 12.0h， 以71%的产率得到cyclooctatetraene-1,4-dicarboxylic acid
  参考文献：
  名称：

  Solvent-induced, selective rearrangement of hydrogen cubane-1,4-dicarboxylate to hydrogen cuneane-2,6-dicarboxylate

  摘要：

  The rearrangement of cubane-1,4-dicarboxylic acid in water to cuneane-2,6-dicarboxylic acid is presented. The reaction is not a transition metal catalyzed, rather a solvent-promoted transformation, and the reaction proceeds via the semi-dissociated form of the cubane diacid, hydrogen cubane-1,4-dicarboxylate. No other, 1,3-disubstituted cuneane isomer is formed. The reaction is significantly accelerated by the addition of 1 equiv of base, suggesting that the hydrogen cubane-1,4-dicarboxylate ion plays a key role in this new type of rearrangement. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.056

文献信息

• Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations
  作者：Sevan D. Houston、Hui Xing、Paul V. Bernhardt、Timothy J. Vanden Berg、John Tsanaktsidis、G. Paul Savage、Craig M. Williams

  DOI：10.1002/chem.201805124

  日期：2019.2.21

  The scope and limitations of Eaton's rhodium(I)‐catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane‐alcohols to undergo one‐pot tandem Ley–Griffith Wittig reactions in the absence of a transition metal catalyst.

  在官能团耐受性，多重取代模式和古巴酒精经历一锅串联Ley-Griffith的能力的背景下，研究了伊顿铑（I）催化的古巴价氢异构化为环辛三烯（COT）的范围和局限性在没有过渡金属催化剂的情况下进行维蒂希反应。