2,3-bis[(E)-2-phenylethenyl]norbornane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,3-bis[(E)-2-phenylethenyl]norbornane
• 英文别名: (1R,2R,3S,4S)-2,3-bis[(E)-2-phenylethenyl]bicyclo[2.2.1]heptane
• 化学式: C₂₃H₂₄
• 分子量: 300.444
• InChiKey: JQQKPCIMSCPIJX-BAMDXCOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 反式-2-苯乙烯硼酸频哪酸酯 在 二(氰基苯)二氯化钯 、 potassium carbonate 、 一氯丙酮 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以72%的产率得到2,3-bis[(E)-2-phenylethenyl]norbornane
  参考文献：
  名称：

  Mizoroki−Heck Type Reaction of Organoboron Reagents with Alkenes and Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)₂ as an Oxidant

  摘要：

  [GRAPHICS]In contrast to the Pd(0)-catalyzed mechanism by Uemura, Mizoroki-Heck type reaction of boronic acids is found to proceed under a Pd(ll)mediated pathway using a catalytic amount of Pd(OAc)(2) in the presence of Cu(OAc)(2) as an oxidant. Treatment of a variety of alkenes with boronic acids, boronates, and sodium tetraphenylborate furnishes beta -arylated and alkenylated products in good to excellent yields. The reactions with norbornene, norbornadiene, and diphenylacetylene are also performed to give 1:2 or 2:1 coupling products.

  DOI：

  10.1021/ol016529y

文献信息

• Novel Palladium-Catalyzed Diarylation and Dialkenylation Reactions of Norbornene Derivatives
  作者：Keigo Fugami、Sachiko Hagiwara、Hiroshi Oda、Masanori Kosugi

  DOI：10.1055/s-1998-1710

  日期：1998.5

  Norbornene and its derivatives are diarylated or dialkenylated by aryl- or alkenyltributylstannanes, a palladium catalyst, and chloroacetone or chloroacetonitrile as a reoxidant.

  降冰片烯及其衍生物通过芳基或烯基三丁基锡烷、钯催化剂以及作为还原剂的氯丙酮或氯乙腈进行二芳基化或二烯丙基化。
• Mizoroki−Heck Type Reaction of Organoboron Reagents with Alkenes and Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)₂ as an Oxidant
  作者：Xiaoli Du、Masahiro Suguro、Kazunori Hirabayashi、Atsunori Mori、Takashi Nishikata、Nobuhito Hagiwara、Kentaro Kawata、Takeaki Okeda、Hui Feng Wang、Keigo Fugami、Masanori Kosugi

  DOI：10.1021/ol016529y

  日期：2001.10.1

  [GRAPHICS]In contrast to the Pd(0)-catalyzed mechanism by Uemura, Mizoroki-Heck type reaction of boronic acids is found to proceed under a Pd(ll)mediated pathway using a catalytic amount of Pd(OAc)(2) in the presence of Cu(OAc)(2) as an oxidant. Treatment of a variety of alkenes with boronic acids, boronates, and sodium tetraphenylborate furnishes beta -arylated and alkenylated products in good to excellent yields. The reactions with norbornene, norbornadiene, and diphenylacetylene are also performed to give 1:2 or 2:1 coupling products.