N-((2-(morpholin-1-yl)cyclohexyl)(phenyl)methyl)-p-toluenesulfonamide

• 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-(morpholin-1-yl)cyclohexyl)(phenyl)methyl)-p-toluenesulfonamide
• 英文别名: 4-methyl-N-[(S)-[(1S,2S)-2-morpholin-4-ylcyclohexyl]-phenylmethyl]benzenesulfonamide
• 化学式: C₂₄H₃₂N₂O₃S
• 分子量: 428.596
• InChiKey: ACPLAUFCJWTDFR-KMDXXIMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-吗啉基-1-环己烯 、 N-亚苄基-4-甲基苯磺酰胺 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 水 、 甲醇 为溶剂， 反应 25.0h， 以40%的产率得到N-((2-(morpholin-1-yl)cyclohexyl)(phenyl)methyl)-p-toluenesulfonamide
  参考文献：
  名称：

  Imino ene-type reaction of enamines with N-sulfonylimines and application to diastereoselective synthesis of N-sulfonyl-1,3-diamines

  摘要：

  Enamines react rapidly with N-sulfonylimines to afford imino ene-type adducts. The reaction proceeds even at -78 degrees C in the presence of acetic acid and shows high diastereoselectivity. Acid hydrolysis of imino ene-type products affords beta-amino ketones, and reduction with NaBH3CN furnishes N-sulfonyl-1,3-diamines with high diastereoselectivities. The stereochemistry of these transformations is considered based on transition state models. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.123

文献信息

• Imino ene-type reaction of enamines with N-sulfonylimines and application to diastereoselective synthesis of N-sulfonyl-1,3-diamines
  作者：Mai Ito、Takeru Kashiwagi、Shunsuke Kotani、Makoto Nakajima、Masaharu Sugiura

  DOI：10.1016/j.tetlet.2014.05.123

  日期：2014.7

  Enamines react rapidly with N-sulfonylimines to afford imino ene-type adducts. The reaction proceeds even at -78 degrees C in the presence of acetic acid and shows high diastereoselectivity. Acid hydrolysis of imino ene-type products affords beta-amino ketones, and reduction with NaBH3CN furnishes N-sulfonyl-1,3-diamines with high diastereoselectivities. The stereochemistry of these transformations is considered based on transition state models. (C) 2014 Elsevier Ltd. All rights reserved.