(E)-2-((2E,4Z)-6-Chloro-hexa-2,4-dienyl)-2,9-bis-methoxycarbonyl-6-methyl-7-oxo-dec-5-enedioic acid dimethyl ester | 290292-46-5

• 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: (E)-2-((2E,4Z)-6-Chloro-hexa-2,4-dienyl)-2,9-bis-methoxycarbonyl-6-methyl-7-oxo-dec-5-enedioic acid dimethyl ester
• 英文别名: tetramethyl (4E,10E,12Z)-14-chloro-4-methyl-3-oxotetradeca-4,10,12-triene-1,1,8,8-tetracarboxylate
• CAS: 290292-46-5
• 化学式: C₂₃H₃₁ClO₉
• 分子量: 486.947
• InChiKey: JBCUWGJMAWTAQE-HNZBGJGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-2-((2E,4Z)-6-Chloro-hexa-2,4-dienyl)-2,9-bis-methoxycarbonyl-6-methyl-7-oxo-dec-5-enedioic acid dimethyl ester 在 氯磺酰异氰酸酯 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以54%的产率得到(3E,5Z,11E)-tetramethyl-11-methyl-10-oxo-3,5,11-cyclotetradecatriene-1,1,8,8-tetracarboxylate
  参考文献：
  名称：

  Transannular Diels–Alder Studies of 14-Membered cis – trans – trans Macrocyclic Trienes Having Allylic Ether or Enone Dienophile

  摘要：

  Highly convergent, malonate alkylation based syntheses of the model macrocycles and their title investigations are reported. In the allylic ether dienophile case, a preference for tricycles with equatorial ether position was found at the transition state level. Ab initio calculations also show that the origin of this preference is not only steric but stereoelectronic as well. The enone dienophile case indicates that when the enone system is not totally twisted out of planarity by the macrocyclic environment, the Diels-Alder reaction follows the usual trend in terms of dienophile activation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00455-5
• 作为产物：
  描述：

  (4E,10E,12Z)-dimethyl-8,8-bis(methoxycarbonyl)-4-methyl-3-oxo-14-tetrahydropyranyloxytetradeca-4,10,12-trienedicarboxylate 在 六氯丙酮 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (E)-2-((2E,4Z)-6-Chloro-hexa-2,4-dienyl)-2,9-bis-methoxycarbonyl-6-methyl-7-oxo-dec-5-enedioic acid dimethyl ester
  参考文献：
  名称：

  Transannular Diels–Alder Studies of 14-Membered cis – trans – trans Macrocyclic Trienes Having Allylic Ether or Enone Dienophile

  摘要：

  Highly convergent, malonate alkylation based syntheses of the model macrocycles and their title investigations are reported. In the allylic ether dienophile case, a preference for tricycles with equatorial ether position was found at the transition state level. Ab initio calculations also show that the origin of this preference is not only steric but stereoelectronic as well. The enone dienophile case indicates that when the enone system is not totally twisted out of planarity by the macrocyclic environment, the Diels-Alder reaction follows the usual trend in terms of dienophile activation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00455-5