(R,R)-N,N'-bissalicyl-N,N'-dimethyl-1,2-diaminocyclohexane | 193824-04-3

• 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: (R,R)-N,N'-bissalicyl-N,N'-dimethyl-1,2-diaminocyclohexane
• 英文别名: 2,2'-[trans-(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]-diphenol；2-[[[(1R,2R)-2-[(2-hydroxyphenyl)methyl-methylamino]cyclohexyl]-methylamino]methyl]phenol
• CAS: 193824-04-3
• 化学式: C₂₂H₃₀N₂O₂
• 分子量: 354.492
• InChiKey: ABYKGWBCLZALOL-WOJBJXKFSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  500.7±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonato)dioxomolybdenum(VI) 、 (R,R)-N,N'-bissalicyl-N,N'-dimethyl-1,2-diaminocyclohexane 以 甲醇 为溶剂， 以40%的产率得到[2,2'-[trans-(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]-diphenolato-O,N,N',O']dioxomolybdenum(VI) trichloromethane solvate
  参考文献：
  名称：

  A Dioxomolybdenum(VI) Complex with a New Enantiomerically Pure Tetrahydrosalen Ligand

  摘要：

  The enantiomerically pure tetradentate Ligand H2L {2,2'-[trans-(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]diphenol} forms a neutral dioxomolyb-denum(VI) complex, which was isolated as {2,2'-[trans(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]- diphenolato-O,N,N',O'}dioxomolybdenum(VI) trichloromethane solvate, [MoO2(C22H28N2O2)].CHCl3, and characterized by a single-crystal X-ray analysis. The coordination geometry around the metal is distorted octahedral. The two oxo O atoms are cis and the two phenolate O atoms are in (distorted) trans positions. The two N atoms are located approximately trans to the oxo O atoms and the Mo-N bonds are remarkably long.

  DOI：

  10.1107/s0108270197003375
• 作为产物：
  描述：

  (1R,2R)-N,N’-di(2-hydroxybenzyl)-1,2-diaminocyclohexane 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以60%的产率得到(R,R)-N,N'-bissalicyl-N,N'-dimethyl-1,2-diaminocyclohexane
  参考文献：
  名称：

  钒-Salan体系催化的硫化物高效不对称氧化和亚砜的动力学拆分

  摘要：

  硫化钒以高收率和高对映选择性将硫化物不对称氧化为手性亚砜已被手性钒-Salan [ N，N'-烷基双（水杨胺）]络合物非常有效地催化。所述salan配体在反应性和对映选择性方面显示出优于salen [ N，N′-亚烷基双（水杨亚基亚胺）]类似物的结果，并提供具有相反构型的亚砜。该反应的高对映选择性是不对称氧化的直接结果。还描述了钒-salan系统催化的外消旋亚砜的有效动力学拆分。

  DOI：

  10.1021/jo040221d
• 作为试剂：
  描述：

  (1R,7S)-cycloheptene oxide 、 苯胺 在 三异丙氧基氧化钒 、 (R,R)-N,N'-bissalicyl-N,N'-dimethyl-1,2-diaminocyclohexane 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1S,2S)-2-(phenylamino)cycloheptan-1-ol 、 (1R,2R)-2-Phenylamino-cycloheptanol
  参考文献：
  名称：

  钒-Salan催化芳族胺对内环氧化物的对映选择性开环

  摘要：

  报道了手性氧钒(V)-salan 配合物催化内消旋环氧化物的对映选择性开环的第一个例子。该反应以良好的收率和中等至高的对映选择性（高达 87%）提供了 1,2-氨基醇。

  DOI：

  10.1055/s-2008-1067109

文献信息

• Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System
  作者：Jiangtao Sun、Chengjian Zhu、Zhenya Dai、Minghua Yang、Yi Pan、Hongwen Hu

  DOI：10.1021/jo040221d

  日期：2004.11.1

  The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide

  硫化钒以高收率和高对映选择性将硫化物不对称氧化为手性亚砜已被手性钒-Salan [ N，N'-烷基双（水杨胺）]络合物非常有效地催化。所述salan配体在反应性和对映选择性方面显示出优于salen [ N，N′-亚烷基双（水杨亚基亚胺）]类似物的结果，并提供具有相反构型的亚砜。该反应的高对映选择性是不对称氧化的直接结果。还描述了钒-salan系统催化的外消旋亚砜的有效动力学拆分。
• Chiral Salan Aluminium Ethyl Complexes and Their Application in Lactide Polymerization
  作者：Hongzhi Du、Aldrik H. Velders、Pieter J. Dijkstra、Jingru Sun、Zhiyuan Zhong、Xuesi Chen、Jan Feijen

  DOI：10.1002/chem.200900799

  日期：2009.9.28

  state, adopting a cis‐(O,O) and cis‐(Me,Me) ligand geometry. From the results of variable‐temperature (VT) 1H NMR in the temperature range of 220–335 K, 1H–1H NOESY at 220 K, and diffusion‐ordered spectroscopy (DOSY), it is concluded that each diastereoisomer b is also monomeric with a five‐coordinated aluminium central core. The geometry is intermediate between square pyramidal with a cis‐(O,O), trans‐(Me

  手性四齿苯氧胺（salan-型）配体支持的铝乙基络合物的合成途径[Al（OC 6 H 2（R-6-R-4）CH 2）2 CH 3 N（C 6 H 10）NCH 3 } -C 2 ħ 5 ]（4，7：R = H; 5，8：R =氯; 6，9：R = CH 3）的报告。在环己烷环上具有（R，R）构型的对映体纯的salan配体1-3提供了配合物4，5，和6 2个非对映异构（作为混合物一和b）。通过X射线分析确定，每个非对映异构体a为固态的五配位铝中心核，呈顺式（O，O）和顺式（Me，Me）配体几何结构。根据220-335 K温度范围内的变温（VT）1 H NMR ，220 K下1 H- 1 H NOESY的结果以及扩散有序光谱法（DOSY）得出的结论是，每个非对映异构体b也是具有五配位铝中心核的单体。几何形状是正方形锥体之间中间体与顺式- （O，O），反式- （ME，ME）配位体配置和三角双锥与反式-
• The first asymmetric addition of organogallium to aldehydes catalyzed by chiral titanium catalysts
  作者：Zhenya Dai、Chengjian Zhu、Minghua Yang、Yunfa Zheng、Yi Pan

  DOI：10.1016/j.tetasy.2004.12.010

  日期：2005.2

  The addition of organogallium to aldehydes was realized with titanium tetrachloride as a Lewis acid catalyst. For the first time, the catalytic asymmetric addition of organogallium to aldehydes was investigated with chiral titanium complexes, which were formed from titanium tetrachloride and salan ligands, with mediocre to good chemical yields and enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.
• A Dioxomolybdenum(VI) Complex with a New Enantiomerically Pure Tetrahydrosalen Ligand
  作者：H. Elias、F. Stock、C. Röhr

  DOI：10.1107/s0108270197003375

  日期：1997.7.15

  The enantiomerically pure tetradentate Ligand H2L 2,2'-[trans-(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]diphenol} forms a neutral dioxomolyb-denum(VI) complex, which was isolated as 2,2'-[trans(R,R)-1,2-cyclohexanediylbis(N-methylaminomethyl)]- diphenolato-O,N,N',O'}dioxomolybdenum(VI) trichloromethane solvate, [MoO2(C22H28N2O2)].CHCl3, and characterized by a single-crystal X-ray analysis. The coordination geometry around the metal is distorted octahedral. The two oxo O atoms are cis and the two phenolate O atoms are in (distorted) trans positions. The two N atoms are located approximately trans to the oxo O atoms and the Mo-N bonds are remarkably long.