(1R,2R)-bis((2,6-dichlorobenzylidene)diamino)cyclohexane | 155324-13-3

• 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: (1R,2R)-bis((2,6-dichlorobenzylidene)diamino)cyclohexane
• 英文别名: 1-(2,6-dichlorophenyl)-N-[(1R,2R)-2-[(2,6-dichlorophenyl)methylideneamino]cyclohexyl]methanimine
• CAS: 155324-13-3
• 化学式: C₂₀H₁₈Cl₄N₂
• 分子量: 428.188
• InChiKey: GWVMFOHLFMAOMJ-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-bis((2,6-dichlorobenzylidene)diamino)cyclohexane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N,N'-bis(2,6-dichlorobenzyl)-(R,R)-1,2-diaminocyclohexane
  参考文献：
  名称：

  Synthesis and structural characterization of a dichloro zinc complex of N,N′-bis-(2,6-dichloro-benzyl)-(R,R)-1,2-diaminocyclohexane: Application to ring opening polymerization of rac-lactide

  摘要：

  A novel dichloro zinc complex (L-1)ZnCl2, where L-1 is N,N'-bis-(2,6-dichloro-benzyl)-(R,R)-1,2-diaminocyclohexane, has been synthesized and characterized. The dimethyl derivatives, generated in situ from the well characterized dichloro zinc complexes (L-1)ZnCl2 and (L-2)ZnCl2, where L-2 is N,N'-bis-(benzyl)-(R,R)-1,2-diaminocyclohexane, were employed as initiators for the ring opening polymerization (ROP) of rac-lactide (rac-LA). The complexes were found to be highly efficient initiators yielding the polylactide (PLA) with a narrow molecular weight distribution. The catalytic activity and heterotactic selectivity of the Zn(II) complexes were affected by the substituents on the phenyl groups of benzyl moieties in (R,R)-1,2-diaminocyclohexane. The dimethyl derivative of (L-2)ZnCl2 produced highly stereocontrolled PLA with P-r = 0.75 at -25 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.10.035
• 作为产物：
  描述：

  2,6-二氯苯甲醛 、 trans-1,2-(R,R)-diammoniumcyclohexane tartrate 在 sodium hydroxide 作用下， 生成 (1R,2R)-bis((2,6-dichlorobenzylidene)diamino)cyclohexane
  参考文献：
  名称：

  Synthesis and structural characterization of a dichloro zinc complex of N,N′-bis-(2,6-dichloro-benzyl)-(R,R)-1,2-diaminocyclohexane: Application to ring opening polymerization of rac-lactide

  摘要：

  A novel dichloro zinc complex (L-1)ZnCl2, where L-1 is N,N'-bis-(2,6-dichloro-benzyl)-(R,R)-1,2-diaminocyclohexane, has been synthesized and characterized. The dimethyl derivatives, generated in situ from the well characterized dichloro zinc complexes (L-1)ZnCl2 and (L-2)ZnCl2, where L-2 is N,N'-bis-(benzyl)-(R,R)-1,2-diaminocyclohexane, were employed as initiators for the ring opening polymerization (ROP) of rac-lactide (rac-LA). The complexes were found to be highly efficient initiators yielding the polylactide (PLA) with a narrow molecular weight distribution. The catalytic activity and heterotactic selectivity of the Zn(II) complexes were affected by the substituents on the phenyl groups of benzyl moieties in (R,R)-1,2-diaminocyclohexane. The dimethyl derivative of (L-2)ZnCl2 produced highly stereocontrolled PLA with P-r = 0.75 at -25 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.10.035
• 作为试剂：
  描述：

  (E)-3-Phenyl-propendithiosaeure-methylester 、 3-丙烯酰基-2-唑烷酮 在 (1R,2R)-bis((2,6-dichlorobenzylidene)diamino)cyclohexane 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 3-((3S,4S)-6-Methylsulfanyl-4-phenyl-3,4-dihydro-2H-thiopyran-3-carbonyl)-3H-oxazol-2-one 、
  参考文献：
  名称：

  The first catalytic, highly enantioselective hetero-Diels–Alder reaction of thiabutadienes

  摘要：

  本研究首次描述了使用同手性铜和镍三酸盐及高氯酸盐双（噁唑啉）和双（亚胺）络合物催化剂对硫杂丁二烯进行催化的高对映选择性杂-DielsâAlder 反应，从而得到具有光学活性的二氢硫代吡喃。

  DOI：

  10.1039/a902076d

文献信息

• Speciation and Mechanistic Studies of Chiral Copper(I) Schiff Base Precursors Mediating Asymmetric Carbenoid Insertion Reactions of Diazoacetates into the Si−H Bond of Silanes
  作者：Les A. Dakin、Patricia C. Ong、James S. Panek、Richard J. Staples、Pericles Stavropoulos

  DOI：10.1021/om0003786

  日期：2000.7.1

  scrambling is observed in competitive carbenoid insertions into PhMe2Si-D/Ph2MeSi-H, indicating that the insertion reaction takes place in a concerted fashion. These results are discussed in light of an early transition state, characterized by hydrogen-first penetration of the Si−H bond into the copper−carbenoid cavity, which is assumed to impart high levels of enantioselectivity due to intrinsic preorganization

  [Cu（CH 3 CN）4 ]（PF 6）和手性C 2对称二亚胺配体（1 R，2 R）-双（（2,6-二氯亚苄基）二氨基）环己烷（R，R - 1）（ 1.2当量）以高至高收率和对映体控制水平介导芳基重氮酸酯不对称类胡萝卜素插入硅烷的Si-H键中。[Cu（CH 3 CN）4 ]（PF 6）/ R，R - 1的二氯甲烷溶液提供黄色结晶的[Cu I（R，R- 1）（CH 3 CN）·铜我（[R ，- [R - 1）（CH 3 CN）2 ·铜我2（[R ，- [R - 1）3 ]（PF 6）4 ·2CH 2氯2 ·3ET 2 O，在晶格中具有三个不同的铜络合物。1 H NMR和电喷雾电离质谱（ESI-MS）研究表明，只有[Cu I（R，R - 1）（CH3 CN）] +高产率地存在于溶液中。添加化学计量的PhC（N 2）CO 2 Me后，阳离子[Cu I（R，R - 1）（C（CO 2 Me）Ph）]
• Discovery of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines: using racemic and achiral diimines as effective activators
  作者：Hua Liu、Hai-Le Zhang、Shuang-Jun Wang、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1016/j.tetasy.2005.07.014

  日期：2005.9

  A library of chiral zinc complexes formed in Situ by the combination of achiral and racemic diimines with 3,3'-di(3,5-ditrifluoromethylphenyl)-BINOL and diethylzinc were evaluated in the asymmetric addition of diethylzine to N-acylimines. In the presence of 10 mol % of chiral ligand 4 and racemic diimine 5, high enantioselectivities of up to 97% ee and yields of up to 96% were achieved for a wide range of aromatic imines in dichloromethane at -30 degrees C. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric Henry reaction catalyzed by chiral secondary diamine-copper(II) complexes
  作者：Rafał Kowalczyk、Łukasz Sidorowicz、Jacek Skarżewski

  DOI：10.1016/j.tetasy.2008.09.032

  日期：2008.10

  The enantioselective Henry reaction was efficiently carried out under mild reaction conditions in 96% ethanol. The chiral C-2-symmetric, secondary bisamines based on the 1,2-diaminocyclohexane framework and copper(II) acetate were found to promote the asymmetric nitroaldol reaction. Aromatic and aliphatic aldehydes were reacted with nitromethane to provide the corresponding beta-nitroalcohols in very good yields and enantioselectivities up to 94%. (C) 2008 Elsevier Ltd. All rights reserved.