N-((1R,2R)-2-aminocyclohexyl)-2,5-dichlorobenzenesulfonamide | 1047662-92-9

• 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)-2,5-dichlorobenzenesulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-2,5-dichlorobenzenesulfonamide
• CAS: 1047662-92-9
• 化学式: C₁₂H₁₆Cl₂N₂O₂S
• 分子量: 323.243
• InChiKey: REKWYIDTFBVSNH-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二氯苄磺酸氯 、 (R,R)-1,2-diaminocyclohexane tartrate 在 sodium hydroxide 、 三乙胺 作用下， 以94%的产率得到N-((1R,2R)-2-aminocyclohexyl)-2,5-dichlorobenzenesulfonamide
  参考文献：
  名称：

  Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane

  摘要：

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.036

文献信息

• Oxygen–chlorine interactions in the transition state of asymmetric Michael additions of carbonyl compounds to β-nitrostyrene
  作者：José A. Romero、Angélica Navarrate、Felipe A. Servín、Domingo Madrigal、Andrew L. Cooksy、Gerardo Aguirre、Daniel Chávez、Ratnasamy Somanathan

  DOI：10.1016/j.tetasy.2014.05.002

  日期：2014.7

  An oxygen-chlorine interaction is reported in the transition state of the Michael addition of acetone to nitrostyrene catalyzed by enantioenriched monosulfonamides. The interaction between the oxygen from the nitro group and the chlorine at the ortho-position of the sulfonamide moiety is supported by theoretical calculations. Asymmetric Michael addition products catalyzed by monosulfonamides were obtained in moderate yields and enantioselectivities. (C) 2014 Elsevier Ltd. All rights reserved.
• Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane
  作者：Norma A. Cortez、Gerardo Aguirre、Miguel Parra-Hake、Ratnasamy Somanathan

  DOI：10.1016/j.tetasy.2008.04.036

  日期：2008.6

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.