N-((1R,2R)-2-aminocyclohexyl)-4-methylbenzamide | 895918-47-5

• 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-((1R,2R)-2-aminocyclohexyl)-4-methylbenzamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-4-methylbenzamide
• CAS: 895918-47-5
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: XONCOGUYTUKBTI-CHWSQXEVSA-N

物化性质

• 沸点：
  414.3±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1R,2R)-2-aminocyclohexyl)-4-methylbenzamide 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (2S,1'R,2'R)-pyrrolidine-2-carboxylic acid [2'-(4-methylbenzamido)-cyclohexyl]-amide
  参考文献：
  名称：

  易于调节和双功能的L-脯氨酰胺衍生物：直接对映选择性Aldol反应的设计和应用。

  摘要：

  [反应：见正文]已开发出易于调节的双功能L-脯氨酰胺作为新型有机催化剂，并在各种芳族醛和环己酮的直接不对称Aldol反应中评估了它们的催化活性。在最佳条件下，获得了高分离产率（高达94％），对映选择性（高达99％ee）和抗非对映选择性（高达99：1）。

  DOI：

  10.1021/ol0520323
• 作为产物：
  描述：

  phenyl N-[(1R,2R)-2-[(4-methylbenzoyl)amino]cyclohexyl]carbamate 在 potassium hydroxide 、 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.17h， 以75%的产率得到N-((1R,2R)-2-aminocyclohexyl)-4-methylbenzamide
  参考文献：
  名称：

  Synthesis of Monoacylated Derivatives of 1,2- Cyclohexanediamine. Evaluation of their Catalytic Activity in the Preparation of Wieland−Miescher Ketone

  摘要：

  Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland-Miescher ketone has been studied with these catalysts.

  DOI：

  10.1021/jo101723v

文献信息

• Chiral amine organocatalysts for the syn-aldol reaction involving substituted benzaldehydes and hydroxyacetone
  作者：Dhruba Sarkar、Kurt Harman、Subrata Ghosh、Allan D. Headley

  DOI：10.1016/j.tetasy.2011.05.021

  日期：2011.5

  A new series of cyclohexanediamine organocatalysts that contain the primary amine functionality has been designed, synthesized and tested as catalysts for the asymmetric aldol reaction involving hydroxyacetone and a variety of substituted benzaldehydes. High enantioselectivites and diasteroselectivites were obtained using catalyst la for these reactions. A key step in this reaction for the formation of the syn-product is the formation of a stable intramolecular hydrogen bonded Z-enamine isomer, which in addition to the steric bulk of the catalyst, serve to dictate the course of the stereochemical outcome of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.
• Readily Tunable and Bifunctional <scp>l</scp>-Prolinamide Derivatives:  Design and Application in the Direct Enantioselective Aldol Reactions
  作者：Jia-Rong Chen、Hai-Hua Lu、Xin-Yong Li、Lin Cheng、Jian Wan、Wen-Jing Xiao

  DOI：10.1021/ol0520323

  日期：2005.9.1

  [reaction: see text] Readily tunable and bifunctional L-prolinamides as novel organocatalysts have been developed, and their catalytic activities were evaluated in the direct asymmetric Aldol reactions of various aromatic aldehydes and cyclohexanone. High isolated yields (up to 94%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) were obtained under the optimal conditions

  [反应：见正文]已开发出易于调节的双功能L-脯氨酰胺作为新型有机催化剂，并在各种芳族醛和环己酮的直接不对称Aldol反应中评估了它们的催化活性。在最佳条件下，获得了高分离产率（高达94％），对映选择性（高达99％ee）和抗非对映选择性（高达99：1）。
• Synthesis of Monoacylated Derivatives of 1,2- Cyclohexanediamine. Evaluation of their Catalytic Activity in the Preparation of Wieland−Miescher Ketone
  作者：Ángel L. Fuentes de Arriba、David G. Seisdedos、Luis Simón、Victoria Alcázar、César Raposo、Joaquín R. Morán

  DOI：10.1021/jo101723v

  日期：2010.12.3

  Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland-Miescher ketone has been studied with these catalysts.