2-methyl-trans-3-methylcyclohex-4-ene-cis-1,2-dicarboxylic anhydride | 82112-10-5

• 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: 2-methyl-trans-3-methylcyclohex-4-ene-cis-1,2-dicarboxylic anhydride
• 英文别名: trans-2,3-dimethylcyclohex-4-ene-cis-1,2-dicarboxylic anhydride
• CAS: 82112-10-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: GIWBIFSEWYWEPT-FWWHASMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-trans-3-methylcyclohex-4-ene-cis-1,2-dicarboxylic anhydride 在 水 作用下， 反应 1.0h， 以52%的产率得到trans-2,3-dimethylcyclohex-4-ene-cis-1,2-dicarboxylic acid
  参考文献：
  名称：

  Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions

  摘要：

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.

  DOI：

  10.1021/ja00094a037
• 作为产物：
  描述：

  柠康酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-methyl-trans-3-methylcyclohex-4-ene-cis-1,2-dicarboxylic anhydride
  参考文献：
  名称：

  Synthesis of Cobalt Substituted 1,3-Diene Complexes with Unusual Structures and Their Exo Selective Diels-Alder Reactions

  摘要：

  The synthesis and characterization (including crystallographic data) of several substituted-pyridine (Rpyr) cobalt bis(dimethylglyoxime) 1,3-butadiene complexes (R = H, tBu, 3,5-diMe, and N,N-dimethylamino) and their Diels-Alder reactions with a variety of dienophiles are reported here. The cobalt-carbon bonds in the Diels-Alder cycloadducts can be cleaved so that cobalt complexes as well as functionalized organic cycloadducts are recovered. Through these cobalt-carbon bond cleavage reactions, cobalt-diene complexes can serve as synthons for a variety of 1,3-dienes such as 1,3-butadiene, 2-(trimethylsiloxy)-1,3-butadiene, iodoprene, (E)-1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (Danishefsky's diene), and 1,2-dichloro-1,3-butadiene. The preparation of several cobalt-substituted 1,2- and 1,3-pentadiene complexes and highly exo-selective Diels-Alder reactions of the 1,3-pentadiene complexes are then discussed followed by demetalation reactions of these more highly substituted cobalt cycloadducts. These demetalation reactions maintain the stereochemical integrity found in the metal cycloadducts and also lead to cobalt recovery.

  DOI：

  10.1021/ja00094a037

文献信息

• Diels-Alder reactions of piperylenes
  作者：Timothy J. Brocksom、Mauricio G. Constantino

  DOI：10.1021/jo00139a013

  日期：1982.8