3c,5-dimethyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride | 39087-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 3c,5-dimethyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride
• 英文别名: 3c,5-Dimethyl-cyclohex-4-en-1r,2c-dicarbonsaeure-anhydrid；(3aR,4R,7aS)-4,6-dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione
• CAS: 39087-16-6；53892-92-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: SKPUPCBFIIMALK-GJMOJQLCSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  122-130 °C(Press: 0.5 Torr)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3c,5-dimethyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride 在 nickel pumice stone-catalyst 作用下， 生成 4,6-二甲基-2-苯并呋喃-1,3-二酮
  参考文献：
  名称：

  Diallyl-3,5-dimethylphthalate polymer

  摘要：

  公开号：

  US02501610A1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 3c,5-dimethyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride
  参考文献：
  名称：

  Bachman; Goebel, Journal of the American Chemical Society, 1942, vol. 64, p. 789

  摘要：

  DOI：

文献信息

• Aqueous Catalysis:  Methylrhenium Trioxide (MTO) as a Homogeneous Catalyst for the Diels−Alder Reaction
  作者：Zuolin Zhu、James H. Espenson

  DOI：10.1021/ja963172y

  日期：1997.4.1

  The title compound proves to be an effective and efficient catalyst for the Diels-Alder reaction when the dienophile is an alpha,beta-unsaturated ketone or aldehyde. It is especially effective in water. Equal amounts of any such dienophile and any of six representative dienes (isoprene, 2-methyl-1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, cyclopentadiene, 1,2,3,4,5-pentamethylcyclopentadiene, and 1,3-cyclohexadiene) were used, along with 1% MTO. The reactions gave usually >90% isolated yield of the cycloaddition product except for the larger dienophiles. Nearly exclusively, there was formed one product isomer, the same one that usually predominates. The reactions were often run in chloroform (mostly) and in other organic solvents. A select number were carried out in water, where the reactions gave a greater product yield in a considerably shorter time. Water, itself, is known to enhance the rates of Diels-Alder reactions, but MTO exerts an additional accelerating effect. Kinetics studies were carried out to show that the rate is proportional to the catalyst concentration. The products do not inhibit the reaction. The desirability of MTO as a Diels-Alder catalyst stems from a combination of favorable properties: the inertness to air/oxygen, the tolerance for many substrates, the use of an aqueous medium, and the absence of product inhibition. The initial step appears to be the (weak) coordination of the carbonyl oxygen to the electropositive rhenium center. Steric crowding around rhenium inhibits reactions of the larger dienophiles.
• Lewina et al., Doklady Akademii Nauk SSSR, 1953, vol. 91, p. 95,97
  作者：Lewina et al.

  DOI：——

  日期：——
• Diallyl-3,5-dimethylphthalate polymer
  申请人：SHELL DEV

  公开号：US02501610A1

  公开（公告）日：1950-03-21
• Bachman; Goebel, Journal of the American Chemical Society, 1942, vol. 64, p. 789
  作者：Bachman、Goebel

  DOI：——

  日期：——