(1R,2R)-N¹-benzyl-N¹-pentylcyclohexane-1,2-diamine | 1523095-80-8

• 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: (1R,2R)-N¹-benzyl-N¹-pentylcyclohexane-1,2-diamine
• 英文别名: (1R,2R)-2-N-benzyl-2-N-pentylcyclohexane-1,2-diamine
• CAS: 1523095-80-8
• 化学式: C₁₈H₃₀N₂
• 分子量: 274.45
• InChiKey: NQAQXZUQJVTBQV-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 19.5h， 生成 (1R,2R)-N¹-benzyl-N¹-pentylcyclohexane-1,2-diamine
  参考文献：
  名称：

  A chiral primary-tertiary-1,2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions

  摘要：

  A novel chiral 1,2-diaminocyclohexane derivative, (1R,2R)-N-1-n-pentyl, N-1-benzyl-1,2-cyclohexanediamine, was designed, synthesized and applied as a catalyst in a number of aldol reactions between ketones and aryl aldehydes. Reactions between acetone and aryl aldehydes gave aldol products with moderate to good yields and with excellent enantioselectivity (up to yield 85%, ee 98%), while reactions between cyclohexanone and aryl aldehydes provided anti-beta-hydroxyketone products with excellent yields, diastereoselectivity and with enantioselectivity (up to 82% yield, anti/syn ratio 99:1, ee 99%). The aldol reactions between acetone and isatins were investigated, which afforded excellent yields and enantioselectivity (up to 95% yield, 98% ee). The (R)- and (S)-isomers of convolutamydine A were obtained with 95% yield and 96% ee, and 95% yield and 94% ee, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.026
• 作为试剂：
  描述：

  5-氟靛红 、 丙酮 在 三氟甲磺酸 、 (1R,2R)-N¹-benzyl-N¹-pentylcyclohexane-1,2-diamine 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以81%的产率得到
  参考文献：
  名称：

  A chiral primary-tertiary-1,2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions

  摘要：

  A novel chiral 1,2-diaminocyclohexane derivative, (1R,2R)-N-1-n-pentyl, N-1-benzyl-1,2-cyclohexanediamine, was designed, synthesized and applied as a catalyst in a number of aldol reactions between ketones and aryl aldehydes. Reactions between acetone and aryl aldehydes gave aldol products with moderate to good yields and with excellent enantioselectivity (up to yield 85%, ee 98%), while reactions between cyclohexanone and aryl aldehydes provided anti-beta-hydroxyketone products with excellent yields, diastereoselectivity and with enantioselectivity (up to 82% yield, anti/syn ratio 99:1, ee 99%). The aldol reactions between acetone and isatins were investigated, which afforded excellent yields and enantioselectivity (up to 95% yield, 98% ee). The (R)- and (S)-isomers of convolutamydine A were obtained with 95% yield and 96% ee, and 95% yield and 94% ee, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.026

文献信息

• A chiral primary-tertiary-1,2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions
  作者：Biao Xu、Lei Li、Shaohua Gou

  DOI：10.1016/j.tetasy.2013.09.026

  日期：2013.12

  A novel chiral 1,2-diaminocyclohexane derivative, (1R,2R)-N-1-n-pentyl, N-1-benzyl-1,2-cyclohexanediamine, was designed, synthesized and applied as a catalyst in a number of aldol reactions between ketones and aryl aldehydes. Reactions between acetone and aryl aldehydes gave aldol products with moderate to good yields and with excellent enantioselectivity (up to yield 85%, ee 98%), while reactions between cyclohexanone and aryl aldehydes provided anti-beta-hydroxyketone products with excellent yields, diastereoselectivity and with enantioselectivity (up to 82% yield, anti/syn ratio 99:1, ee 99%). The aldol reactions between acetone and isatins were investigated, which afforded excellent yields and enantioselectivity (up to 95% yield, 98% ee). The (R)- and (S)-isomers of convolutamydine A were obtained with 95% yield and 96% ee, and 95% yield and 94% ee, respectively. (C) 2013 Elsevier Ltd. All rights reserved.