(Z)-3-(4-methoxyphenyl)-2-propyl-2-hexenenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3-(4-methoxyphenyl)-2-propyl-2-hexenenitrile
• 英文别名: (Z)-3-(4-methoxyphenyl)-2-propylhex-2-enenitrile
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: ZPHAFZVWBZNBPY-PEZBUJJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-辛炔 、 4-甲氧基苯甲腈 在 dichlorobis(dimethylphenylphosphine)nickel(II) 、 三甲基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 19.0h， 以96%的产率得到(Z)-3-(4-methoxyphenyl)-2-propyl-2-hexenenitrile
  参考文献：
  名称：

  Nickel/Lewis Acid-Catalyzed Aryl- and Alkenylcyanation of Unsaturated Bonds

  摘要：

  路易斯酸共催化剂，如有机铝和有机硼化合物，显著提高了镍催化的炔烃芳腈化反应的效率。在没有路易斯酸的情况下表现出较差反应性的富电子芳腈，在镍/路易斯酸双重催化下顺利进行芳腈化反应。对于带有氯或溴基团的芳腈，观察到优异的化学选择性，从而可以一步合成P-3622的合成中间体，一种蔗糖合成酶抑制剂。芳腈化反应的适用范围也扩展到诺尔苯二烯。在镍/路易斯酸双重催化下实现了对炔烃的烯炔腈化反应，选择性地生成氰基取代的1,3-二烯。

  DOI：

  10.1246/bcsj.20100068

文献信息

• Nickel-Catalyzed Arylcyanation of Alkynes
  作者：Yoshiaki Nakao、Shinichi Oda、Tamejiro Hiyama

  DOI：10.1021/ja0448723

  日期：2004.11.1

  A nickel catalyst coordinated by trimethylphosphine is found to effect the addition reaction of Ar-CN bonds in aromatic nitriles across alkynes to give rise to various beta-arylalkenenitriles.
• Arylcyanation of alkynes catalyzed by nickel
  作者：Yoshiaki Nakao、Shinichi Oda、Akira Yada、Tamejiro Hiyama

  DOI：10.1016/j.tet.2006.02.086

  日期：2006.8

  A nickel catalyst prepared from Ni(cod)(2) and PMe3 is found to effect arylcyanation reaction of alkynes. namely cleavage of a C-CN bond of an aryl cyanide followed by addition of each fragment across an alkyne. A wide range of functional groups in aryl cyanides tolerated the catalysis, giving variously functionalized beta-arylalkenenitriles stereoselectively. (c) 2006 Elsevier Ltd. All rights reserved.
• A Dramatic Effect of Lewis-Acid Catalysts on Nickel-Catalyzed Carbocyanation of Alkynes
  作者：Yoshiaki Nakao、Akira Yada、Shiro Ebata、Tamejiro Hiyama

  DOI：10.1021/ja067364x

  日期：2007.3.1

  Lewis-acid catalysts such as AlMe3, AlMe2Cl, and BPh3 significantly improve the efficiency of the nickel-catalyzed arylcyanation of alkynes. Electron-rich aryl cyanides, which exhibit poor reactivity in the absence of Lewis acids, readily undergo the arylcyanation reaction under the newly disclosed conditions. Excellent chemoselectivity is observed for aryl cyanides having a chloro and bromo group, allowing a single-step preparation of the synthetic intermediate of P-3622, a squalene synthetase inhibitor. Moreover, the first examples of alkenyl- and alkylcyanation of alkynes have been achieved by the nickel-Lewis acid dual catalyst.