rac-N-(cyclohex-2-enyl)-N-phenylacetamide | 1260208-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-N-(cyclohex-2-enyl)-N-phenylacetamide
• CAS: 1260208-15-8
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: HAFDRQZWSQPDHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  rac-N-(cyclohex-2-enyl)-N-(2-iodophenyl)acetamide 在 三乙基硼 、 三正丁基氢锡 作用下， 以 正己烷 、 苯 为溶剂， 反应 0.08h， 以10%的产率得到rac-N-(cyclohex-2-enyl)-N-phenylacetamide
  参考文献：
  名称：

  Radical and Heck Cyclizations of Diastereomeric o-Haloanilide Atropisomers

  摘要：

  The outcomes of radical cyclizations and Heck reactions of N-(cyclohex-2-enyl)-N-(2-iodophenyl)acetamides depend critically on the configurations of the chiral axis and the stereocenter. In substrates without an or-rho-methyl group, the diastereomeric precursors interconvert slowly at ambient temperatures. Cyclization of enriched mixtures of diastereomers provided similar yields of acetyl tetrahydrocarbazoles or dihydrocarbazoles, suggesting that interconversion of the radical or organometallic intermediates also occurs. Diastereomers of N-(cyclohex-2-enyl)-N-(2-iodo-4,6-dimethylphenyl)acetamides with an additional ortnomethyl group did not interconvert at ambient temperatures and were readily resolved. In radical cyclizations, syn diastereomers were prone to cyclize, while anti isomers were not. Strikingly, Heck reactions gave the opposite result; anti isomers were prone to cyclization and syn isomers were not. Heck reactions of allylic acetates occur with beta-hydride elimination when acetate is trans to palladium and with beta-acetoxy elimination when acetate is cis. This is surprising because prior studies have suggested that a trans relationship of palladium and acetoxy is essential for acetate elimination. Analyses of the results provide insights into mechanisms for radical cyclization and for insertion and elimination in the Heck reaction.

  DOI：

  10.1021/ja108795x

文献信息

• 一种制备烯丙基胺类化合物的方法
  申请人：苏州大学

  公开号：CN107935860B

  公开（公告）日：2019-09-10

  本发明公开了一种制备烯丙基胺类化合物的方法，即以分子式为[(RNCH2CH2NR)CH][FeBr4]（R为叔丁基）的含1,3‑二叔丁基咪唑啉阳离子的离子型铁（III）配合物为催化剂、以过氧化二叔丁基为氧化剂，通过胺类化合物与烯丙基烃类化合物的氧化偶联反应来合成烯丙基胺类化合物。本发明适用范围广，不仅用于含有吸电子基团的芳香族胺，而对于含有供电子基团的芳香族胺也有效,这是由铁系催化剂实现的经胺类化合物和烯丙基烃类化合物的氧化偶联反应来制备烯丙基胺类化合物的第一例。