(+/-)-trans-N-(2-cyano-cyclopentyl)-benzamide

• 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: (+/-)-trans-N-(2-cyano-cyclopentyl)-benzamide
• 英文别名: N-[(1S,2S)-2-cyanocyclopentyl]benzamide
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: AWVSUGIQUMUIQO-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 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：
  0.38
• 拓扑面积：
  52.89
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-N-(2-cyano-cyclopentyl)-benzamide 在 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 trans-N-(2-carbamoyl-cyclopentyl)-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：

  己二腈 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydride 、 sodium cyanoborohydride 、 magnesium 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 8.5h， 生成 (+/-)-trans-N-(2-cyano-cyclopentyl)-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

文献信息

• A One-Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes
  作者：James L. Collins、Daryl Staveness、Madison J. Sowden、Corey R. J. Stephenson

  DOI：10.1021/acs.orglett.2c01483

  日期：2022.6.24

  cyclopropylimines and substituted alkenes to generate aminocyclopentane derivatives. The Schiff base of the cyclopropylimine was designed to enable a masked N-centered radical approach in which the requisite open-shell character was achieved upon excitation with visible light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via solvolysis and N-acylation. The photochemical

  本文详细描述了环丙亚胺和取代的烯烃之间的光化学分子间形式[3+2]环加成以生成氨基环戊烷衍生物的发展。环丙亚胺的席夫碱旨在实现掩蔽的 N 中心自由基方法，其中在可见光激发下实现所需的开壳层特征。环加成产物通过溶剂解和N-酰化直接转化为N-官能化氨基环戊烷。该反应序列的光化学成分被证明可以在连续流中运行。
• Synthesis and microbial transformation of β-amino nitriles
  作者：Margit Winkler、Ludmila Martínková、Astrid C. Knall、Stefan Krahulec、Norbert Klempier

  DOI：10.1016/j.tet.2005.02.057

  日期：2005.4

  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.