(2E,4Z)-3-tert-Butyl-6,6-dimethyl-2,4-heptadienal | 168071-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4Z)-3-tert-Butyl-6,6-dimethyl-2,4-heptadienal
• 英文别名: (2E,4Z)-3-tert-butyl-6,6-dimethylhepta-2,4-dienal
• CAS: 168071-68-9
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: LMGQRLRSBCBIOR-BYSFRFKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 (2E,4Z)-3-tert-Butyl-6,6-dimethyl-2,4-heptadienal 在 4 A molecular sieve 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 tert-Butyl-[(2E,4Z)-3-tert-butyl-6,6-dimethyl-hepta-2,4-dien-(E)-ylidene]-amine
  参考文献：
  名称：

  6.pi.-Electrocyclization of 1-Azatrienes to 1,2-Dihydropyridines

  摘要：

  A series of alpha,beta-cis-dienals were synthesized by oxidation and then in situ isomerization of easily available beta-allenic alcohols. Subsequent reaction between the alpha,beta-cis-dienals and primary amines represents a simple and useful method for the direct preparation of 1,2-dihydropyridines. Reactivity profiles and activation parameters for the cyclization of alpha,beta-cis-dienimines are similar to those of the carbocyclic counterparts except the reaction is much faster. Despite the lack of a clear stereochemical label, the disrotatory nature of the ring closure is illustrated by the greater cyclization rates of 8'c and 8'd as compared to 7'c and 7'd, respectively. The observation that sterically more hindered systems (8'c and 8'd) cyclize faster than less hindered ones (7'c and 7'd) is a feature of 6 pi-electrocyclizations that is unprecedented.

  DOI：

  10.1021/jo00111a039
• 作为产物：
  描述：

  (2E,4Z)-3-tert-Butyl-6,6-dimethylhepta-2,4-dien-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到(2E,4Z)-3-tert-Butyl-6,6-dimethyl-2,4-heptadienal
  参考文献：
  名称：

  6.pi.-Electrocyclization of 1-Azatrienes to 1,2-Dihydropyridines

  摘要：

  A series of alpha,beta-cis-dienals were synthesized by oxidation and then in situ isomerization of easily available beta-allenic alcohols. Subsequent reaction between the alpha,beta-cis-dienals and primary amines represents a simple and useful method for the direct preparation of 1,2-dihydropyridines. Reactivity profiles and activation parameters for the cyclization of alpha,beta-cis-dienimines are similar to those of the carbocyclic counterparts except the reaction is much faster. Despite the lack of a clear stereochemical label, the disrotatory nature of the ring closure is illustrated by the greater cyclization rates of 8'c and 8'd as compared to 7'c and 7'd, respectively. The observation that sterically more hindered systems (8'c and 8'd) cyclize faster than less hindered ones (7'c and 7'd) is a feature of 6 pi-electrocyclizations that is unprecedented.

  DOI：

  10.1021/jo00111a039