di-(Z)-hex-2-enyl fumarate | 1009734-92-2

• 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: di-(Z)-hex-2-enyl fumarate
• 英文别名: bis[(Z)-hex-2-enyl] (E)-but-2-enedioate
• CAS: 1009734-92-2
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: XZFAQUKINMSMRO-HKTUPRFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  di-(Z)-hex-2-enyl fumarate 、 diethylzinc 、 硫酸二甲酯 在 Cu(N-tBu*sal)2 三甲基氯硅烷 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 6.0h， 以78%的产率得到
  参考文献：
  名称：

  Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates:  Simple Access to Terminally Differentiated Succinates

  摘要：

  The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.

  DOI：

  10.1021/jo701778k
• 作为产物：
  描述：

  顺-2-己烯-1-醇 、 反丁烯二酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到di-(Z)-hex-2-enyl fumarate
  参考文献：
  名称：

  Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates:  Simple Access to Terminally Differentiated Succinates

  摘要：

  The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.

  DOI：

  10.1021/jo701778k

文献信息

• Conjugate Addition/Ireland−Claisen Rearrangements of Allyl Fumarates:  Simple Access to Terminally Differentiated Succinates
  作者：Cory C. Bausch、Jeffrey S. Johnson

  DOI：10.1021/jo701778k

  日期：2008.2.1

  The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.