(2E,4E)-hexa-2,4-dien-1-yl Z-crotonate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E)-hexa-2,4-dien-1-yl Z-crotonate
• 英文别名: [(2E,4E)-hexa-2,4-dienyl] (Z)-but-2-enoate
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: GRIQVJDRCQPNRS-CZZCMEDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-hexa-2,4-dien-1-yl Z-crotonate 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 反应 21.0h， 以31%的产率得到(+/-)-(3aS,6R,7S,7aS)-6,7-dimethyl-3,3a,6,7,7a-hexahydro-7-isobenzofuran-1-one
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes

  摘要：

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.

  DOI：

  10.1021/jo0505829
• 作为产物：
  描述：

  (2E,4E)-2,4-己二烯-1-醇 、 异巴豆酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以11%的产率得到(2E,4E)-hexa-2,4-dien-1-yl Z-crotonate
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes

  摘要：

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.

  DOI：

  10.1021/jo0505829

文献信息

• Cannabinoid receptor modulators
  申请人：Chackalamannil Samuel

  公开号：US20070197628A1

  公开（公告）日：2007-08-23

  A compound having the general structure of Formula (I): or a pharmaceutically acceptable salt, solvate, or ester thereof, is useful in treating diseases, disorders, or conditions such as obesity, metabolic disorders, addiction, diseases of the central nervous system, cardiovascular disorders, respiratory disorders, and gastrointestinal disorders.

  具有通式（I）的一种化合物：或其药用盐、溶剂合物或酯，可用于治疗肥胖、代谢紊乱、成瘾、中枢神经系统疾病、心血管疾病、呼吸系统疾病和消化系统疾病等疾病、紊乱或症状。
• US7897601B2
  申请人：——

  公开号：US7897601B2

  公开（公告）日：2011-03-01
• Intramolecular Diels−Alder Reactions of Ester-Linked 1,3,8-Nonatrienes
  作者：Tory N. Cayzer、Michael N. Paddon-Row、Damian Moran、Alan D. Payne、Michael S. Sherburn、Peter Turner

  DOI：10.1021/jo0505829

  日期：2005.7.1

  Penta-1,3-dienyl acrylates undergo kinetically controlled intramolecular Diels-Alder (lMDA) reactions and DFT calculations (B3LYP/6-31+G(d)) predict stereoselectivities that are in very good agreement with the experimental values. The nature of the diene Cl substituent has virtually no influence upon reactivity or trans/cis-stereoselectivity whereas terminal C9 dienophile substituents have a substantial effect on both the reactivity and stereoselectivity of these IMDA reactions. The TSs highlight contributions from strain in the developing tether-containing ring, and steric and electronic effects between tether and dienophile substituents, thus providing insight into the origins of IMDA reactivity and stereoselectivity.