(1R,2R)-N-(N,N-dimethylsulfamoyl)-1,2-cyclohexanediamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-N-(N,N-dimethylsulfamoyl)-1,2-cyclohexanediamine
• 英文别名: (1R,2R)-N-(N,N-dimethylsulfamoyl)-1,2-diaminocyclohexane；(1R,2R)-1-amino-2-(dimethylsulfamoylamino)cyclohexane
• 化学式: C₈H₁₉N₃O₂S
• 分子量: 221.324
• InChiKey: JYFIGVCFPPEMQL-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲胺基磺酰氯 、 (1R,2R)-(+)-1,2-环己二胺 L-酒石酸盐 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到(1R,2R)-N-(N,N-dimethylsulfamoyl)-1,2-cyclohexanediamine
  参考文献：
  名称：

  水溶性手性单磺酰胺-环己烷-1，2-二胺-RhCp *配合物及其在酮的不对称转移氢化中的应用

  摘要：

  具有杂原子/杂环系统的单磺酰胺配体衍生自反式-（1 R，2 R）-环己烷-1,2-二胺，并与[Ru（苯）Cl 2 ] 2，[Cp ∗ RhCl 2 ] 2原位复合，用于以甲酸钠水溶液为氢源的芳香族酮的ATH。以＞ 93％的对映选择性和＞ 89％的产率获得手性仲醇。水中的还原比异丙醇/ KOH中的还原更快。表面活性剂的添加显示很少或没有效果。

  DOI：

  10.1016/j.tetlet.2007.04.116

文献信息

• New chiral Schiff base–zinc complexes and their esterolytic catalytic activity
  作者：Ramu Kannappan、Masaomi Matsumoto、John Hallren、Kenneth M. Nicholas

  DOI：10.1016/j.molcata.2011.02.014

  日期：2011.4

  A new series of chiral Zn-Schiff base (imine) complexes has been prepared from mono-N-sulfonyl derivatives of (1R,2R)-diaminocyclohexane, N-heterocyclic aldehydes, and zinc salts. The formation and characterization of the (L)ZnX2 complexes was established by NMR. IR and HRESI-MS. Spectroscopic and kinetic evidence indicates that these ligands may be bidentate or tridentate depending on conditions of the medium. The methanolysis of a chiral, racemic picolinate ester catalyzed by the Zn(II)-Schiff base complexes was studied kinetically. The rate constants were found to vary approximately a hundred-fold and in a complex way depending on the imine ligand and the Zn-counter anion, k(obs) =5.0 x 10(-6)-4.8 x 10(-4) M-1 s(-1). A Job plot analysis of ternary complex formation of LZnX2 with two phosphonate transition state analogs suggests that two types of (imine)Zn(picolinate)X ternary complexes may be intermediates and that varying rate-limiting steps may be involved in the LZnX2-catalyzed methanolysis of picolinate esters. (C) 2011 Elsevier B.V. All rights reserved.
• Water-soluble chiral monosulfonamide-cyclohexane-1,2-diamine-RhCp∗ complex and its application in the asymmetric transfer hydrogenation (ATH) of ketones
  作者：Norma A. Cortez、Gerardo Aguirre、Miguel Parra-Hake、Ratnasamy Somanathan

  DOI：10.1016/j.tetlet.2007.04.116

  日期：2007.6

  Monosulfonamide ligands with heteroatom/heterocyclic systems were derived from trans-(1R,2R)-cyclohexane-1,2-diamine and complexed with [Ru(benzene)Cl2]2, [Cp∗RhCl2]2 in situ and used in the ATH of aromatic ketones with aqueous sodium formate as the hydrogen source. The chiral secondary alcohols were obtained with >93% enantioselectivity and >89% yield. Reduction in water was faster than in isopropanol/KOH

  具有杂原子/杂环系统的单磺酰胺配体衍生自反式-（1 R，2 R）-环己烷-1,2-二胺，并与[Ru（苯）Cl 2 ] 2，[Cp ∗ RhCl 2 ] 2原位复合，用于以甲酸钠水溶液为氢源的芳香族酮的ATH。以＞ 93％的对映选择性和＞ 89％的产率获得手性仲醇。水中的还原比异丙醇/ KOH中的还原更快。表面活性剂的添加显示很少或没有效果。