(3E,8E)-9,11-Dimethyl-1,3,8,10-dodecatetraene | 130575-54-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (3E,8E)-9,11-Dimethyl-1,3,8,10-dodecatetraene
• 英文别名: (3E,8E)-9,11-dimethyldodeca-1,3,8,10-tetraene
• CAS: 130575-54-1
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: KMWFPYIXQQWUPN-WXGDJGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3E,8E)-9,11-Dimethyl-1,3,8,10-dodecatetraene 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以27%的产率得到<4aS*,9aR*>-2,4a,5,6,7,8,9,9a-Octahydro-1,1-dimethyl-9-methylene-1H-benzocycloheptene
  参考文献：
  名称：

  在分子内离子 Diels-Alder 反应中使用烷基取代来控制环大小

  摘要：

  双环 [4.3.0] 壬基、双环 [4.4.0] 癸基或双环 [5.4.0] 十一烷基环系统可以从 1,3,8,10-十一碳四烯通过甲基取代、酸催化剂、和温度。这对于不易获得的双环 [5.4.0] 十一烷特别有用

  DOI：

  10.1021/ja00179a079

文献信息

• Use of alkyl substitution to control ring size in the intramolecular ionic Diels-Alder reaction
  作者：Paul G. Gassman、David B. Gorman

  DOI：10.1021/ja00179a079

  日期：1990.11

  The bicyclo [4.3.0] nonyl, bicyclo [4.4.0] decyl or bicyclo [5.4.0] undecyl ring systems can be produced from 1,3,8,10-undecatetraene through a judicious choice of methyl substitution, acid catalyst, and temperature. This is particularly useful in the case of the bicyclo [5.4.0] undecanes, which are not readily available

  双环 [4.3.0] 壬基、双环 [4.4.0] 癸基或双环 [5.4.0] 十一烷基环系统可以从 1,3,8,10-十一碳四烯通过甲基取代、酸催化剂、和温度。这对于不易获得的双环 [5.4.0] 十一烷特别有用
• Influence of Alkyl Substitution on the Intramolecular Ionic Diels-Alder Reaction of Tetraenes
  作者：David B. Gorman、Paul G. Gassman

  DOI：10.1021/jo00109a032

  日期：1995.2

  Fifteen tetraenes, comprised primarily of methylated analogs of (3E,8E)-1,3,8,10-undecatetraene, were synthesized and treated with acid to study the influence of alkyl substitution on the intramolecular ionic Diels-Alder reaction. Depending on methyl substitution patterns of these tetraenes, bicyclo[4.3.0]nonyl, bicyclo[4.4.0]decyl, and bicyclo[5.4.0]undecyl ring systems were produced. For two tetraenes, the ring preference between two different Diels-Alder-derived ring skeletons could be controlled using different temperatures and acid catalysts. Mechanistically, a stepwise process was postulated for at least some of these Diels-Alder reactions. The irreversible and stereoselective formation of the same Diels-Alder product from two noninterconverting tetraenes, which differed only by the cis-trans relationship of a terminal methyl group, was best explained by a stepwise process. A stepwise process was best demonstrated when intermediate triene products isolated from a reaction mixture irreversibly cyclized to Diels-Alder products when resubmitted to the reaction conditions. Although several of the tetraenes failed to give significant amounts of Diels-Alder products, certain alkyl substitution patterns were identified which generally led to high yields of cyclized products.