cis-2-(tert-butoxycarbonylamino)cyclohexanecarbonitrile | 874293-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-2-(tert-butoxycarbonylamino)cyclohexanecarbonitrile
• 英文别名: rel-1,1-Dimethylethyl N-[(1R,2S)-2-cyanocyclohexyl]carbamate；tert-butyl N-[(1S,2R)-2-cyanocyclohexyl]carbamate
• CAS: 874293-99-9
• 化学式: C₁₂H₂₀N₂O₂
• 分子量: 224.303
• InChiKey: BBMSADVUENDKHR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.12
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-2-(tert-butoxycarbonylamino)cyclohexanecarbonitrile 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 (1R,2S)-2-Amino-cyclohexanecarbonitrile; compound with trifluoro-acetic acid
  参考文献：
  名称：

  An effective approach to the enantiomers of alicyclic β-aminonitriles by using lipase catalysis

  摘要：

  Lipase-catalyzed N-acylations of racemic cis- and trans-2-aminocyclopentane- (and cyclohexane-) carbonitriles with 2,2,2-trifluoethyl butanoate in tert-butyl methyl ether (TBME) and in room-temperature ionic liquids (RTILs) were studied. The racemates were effectively resolved (E > 200) on a preparative scale by lipase PS-C II (lipase from Burkholderia cepacia) in TBME, resulting in two enantiomers in their enantiopure forms at 50% conversion. The reactions in RTILs with Novozym 435 (Candida antarctica lipase B) were slow and proceeded with low enantio selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.017
• 作为产物：
  描述：

  7-tert-butoxycarbonyl-7-azabicyclo[4,2,0]hexan-8-one 在 氨 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 cis-2-(tert-butoxycarbonylamino)cyclohexanecarbonitrile
  参考文献：
  名称：

  An effective approach to the enantiomers of alicyclic β-aminonitriles by using lipase catalysis

  摘要：

  Lipase-catalyzed N-acylations of racemic cis- and trans-2-aminocyclopentane- (and cyclohexane-) carbonitriles with 2,2,2-trifluoethyl butanoate in tert-butyl methyl ether (TBME) and in room-temperature ionic liquids (RTILs) were studied. The racemates were effectively resolved (E > 200) on a preparative scale by lipase PS-C II (lipase from Burkholderia cepacia) in TBME, resulting in two enantiomers in their enantiopure forms at 50% conversion. The reactions in RTILs with Novozym 435 (Candida antarctica lipase B) were slow and proceeded with low enantio selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.017