N-(2-cyano-cyclohex-1-enyl)-benzamide | 852379-07-8

• 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: N-(2-cyano-cyclohex-1-enyl)-benzamide
• 英文别名: N-(2-cyanocyclohexen-1-yl)benzamide
• CAS: 852379-07-8
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: ZPBFIBQFSUMGTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-cyano-cyclohex-1-enyl)-benzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 72.0h， 生成 (+/-)-cis-N-(2-cyano-cyclohexyl)-benzamide
  参考文献：
  名称：

  Synthesis and microbial transformation of β-amino nitriles

  摘要：

  Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce beta-amino amides and acids from beta-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitrites gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.057
• 作为产物：
  描述：

  1,5-二氰基戊烷 在 吡啶 、 sodium hydride 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 N-(2-cyano-cyclohex-1-enyl)-benzamide
  参考文献：
  名称：

  Synthesis and microbial transformation of β-amino nitriles

  摘要：

  Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce beta-amino amides and acids from beta-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitrites gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.057