(3Z,5E,11Z)-11-Methyl-cyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylic acid tetramethyl ester | 117832-81-2

• 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: (3Z,5E,11Z)-11-Methyl-cyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylic acid tetramethyl ester
• 英文别名: tetramethyl (3Z,5E,11Z)-11-methylcyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylate
• CAS: 117832-81-2
• 化学式: C₂₃H₃₂O₈
• 分子量: 436.502
• InChiKey: RDNUWAQOLRKBFQ-HZENZMRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3Z,5E,11Z)-11-Methyl-cyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylic acid tetramethyl ester 以89%的产率得到
  参考文献：
  名称：

  LAMOTHE, SERGE;NDIBWAMI, ALEXIS;DESLONGCHAMPS, PIERRE, TETRAHEDRON LETT., 29,(1988) N 14, 1641-1644

  摘要：

  DOI：
• 作为产物：
  描述：

  tetramethyl (4Z,10E,12Z)-14-chloro-5-methyltetradeca-4,10,12-triene-1,1,8,8-tetracarboxylate 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3Z,5E,11Z)-11-Methyl-cyclotetradeca-3,5,11-triene-1,1,8,8-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Ndibwami, Alexis; Lamothe, Serge; Soucy, Pierre, Canadian Journal of Chemistry, 1993, vol. 71, # 5, p. 714 - 725

  摘要：

  DOI：

文献信息

• Increasing the Efficiency of the Transannular Diels−Alder Strategy via Stille Macrocyclizations
  作者：Eric Marsault、Pierre Deslongchamps

  DOI：10.1021/ol000209h

  日期：2000.10.1

  [GRAPHICS]To increase the potential and flexibility of the transannular Diels-Alder strategy to build tricycles and tetracycles, the synthesis of macrocyclic trienes of defined geometries has been approached via Stille macrocyclization, giving very high yield and purity of the desired macrocycles or tricycles.
• LAMOTHE, SERGE;NDIBWAMI, ALEXIS;DESLONGCHAMPS, PIERRE, TETRAHEDRON LETT., 29,(1988) N 14, 1641-1644
  作者：LAMOTHE, SERGE、NDIBWAMI, ALEXIS、DESLONGCHAMPS, PIERRE

  DOI：——

  日期：——
• Experimental and Semiempirical Calculation Studies of Transannular Diels-Alder and Other Competing Pericyclic Reactions
  作者：Yves L. Dory、Pierre Soucy、Marc Drouin、Pierre Deslongchamps

  DOI：10.1021/ja00106a060

  日期：1995.1

  Several related macrocyclic trienes have been found to interconvert thermally via [1,5]sigmatropic hydrogen shifts at the diene sites. These macrocyclic trienes further undergo thermal transannular Diels-Alder cycloaddition, thus yielding complex mixtures of adducts. This difficult problem has been tackled and qualitatively solved by means of the semiempirical methods AM1 and PM3. Most of the starting material ground states have been characterized as well as all the [1,5]sigmatropic hydrogen shift and Diels-Alder transition structures. The results of these calculations indicate that some [1,5]sigmatropic hydrogen shift enthalpies of activation are within the same range of most Diels-Alder enthalpies of activation. As a result the Curtin-Hammett principle does not apply for the entire system but only on limited regions. The method proved successful in uncovering the previously missassigned identity of one of the Diels-alder adducts: an unexpected 5-6-7-membered tricycle.
• Ndibwami, Alexis; Lamothe, Serge; Soucy, Pierre, Canadian Journal of Chemistry, 1993, vol. 71, # 5, p. 714 - 725
  作者：Ndibwami, Alexis、Lamothe, Serge、Soucy, Pierre、Goldstein, Solo、Deslongchamps, Pierre

  DOI：——

  日期：——