N,N'-bis(2,6-dichlorobenzyl)-(R,R)-1,2-diaminocyclohexane | 1093871-59-0

• 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,N'-bis(2,6-dichlorobenzyl)-(R,R)-1,2-diaminocyclohexane
• CAS: 1093871-59-0
• 化学式: C₂₀H₂₂Cl₄N₂
• 分子量: 432.22
• InChiKey: GNPZUMUJPDTHHM-WOJBJXKFSA-N

物化性质

• 熔点：
  156-157 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  526.7±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,6-dichlorobenzyl)-(R,R)-1,2-diaminocyclohexane 、 zinc(II) chloride 以 乙醇 为溶剂， 以87%的产率得到dichloro[N,N'-bis(2,6-dichlorobenzyl)-(R,R)-1,2-diaminocyclohexane]zinc(II)
  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：

  (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

文献信息

• Machine‐Assisted Preparation of a Chiral Diamine Ligand Library and In Silico Screening Using Ab Initio Structural Parameters for Heterogeneous Chiral Catalysts
  作者：Tatsuya Kuremoto、Ren Sadatsune、Tomohiro Yasukawa、Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1002/adsc.202100798

  日期：2021.9.7

  containing 31 chiral diamines was synthesized using a flow-based semiautomatic reductive amination system. These ligands were evaluated in a continuous-flow asymmetric 1,4-addition reaction with a heterogeneous Ni catalyst. Based on the experimental results of ab initio DFT calculations, a prediction model for enantioselectivities was successfully constructed. Furthermore, virtual screening of possible ligands

  使用基于流动的半自动还原胺化系统合成了包含 31 个手性二胺的配体库。这些配体在与非均相 Ni 催化剂的连续流动不对称 1,4-加成反应中进行了评估。基于 ab initio DFT 计算的实验结果，成功构建了对映选择性的预测模型。此外，对可能的配体进行虚拟筛选以鉴定有希望的结构，其在实验中显示出良好的对映选择性。
• 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.