(1R,2R)-N1,N2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine | 861860-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2R)-N1,N2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine
• 英文别名: (1R,2R)-N ¹,N ²-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine
• CAS: 861860-60-8
• 化学式: C₂₈H₃₀N₂
• 分子量: 394.56
• InChiKey: NPBFYYBSTMWIHK-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (1R,2R)-N1,N2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine 、 zinc(II) chloride 以 乙醇 为溶剂， 反应 12.0h， 以91%的产率得到[Zn((1R,2R)-N ¹,N ²-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine)Cl₂]
  参考文献：
  名称：

  Synthesis, structure and photoluminescence properties of naphthalene-based chiral zinc(II) complexes

  摘要：

  Two novel chiral zinc(II) complexes containing naphthalene moieties, namely [Zn(CMN)Cl-2] (1) and [Zn (CBN)Cl-2] (2), were obtained through the reaction of zinc(II) chloride with, respectively, (1R,2R)-N-1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (CMN) and (1R,2R)-N-1,N-2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (CBN) in ethanol. The ligands CMN and CBN were characterized via infrared, nuclear magnetic resonance and absorption spectroscopic analyses. As regards to the two complexes, a comprehensive single crystal X-ray diffraction investigation showed that in both cases the zinc (II) ion is surrounded by two N atoms of CMN/CBN and two chloro groups, and has a distorted tetrahedral structure, though 2 also contains an additional naphthalene group. The photo-physical properties of 1 and 2 were examined based on their electronic absorption and photoluminescence spectra. Both complexes exhibited ultraviolet emissions (both at 335 nm in CHCl3; 336 and 385 nm for 1 and 337 nm for 2 in their solid states) under 278-298 nm excitation. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2020.114643
• 作为产物：
  描述：

  1-naphthalen-2-yl-N-[(1R,2R)-2-(naphthalen-2-ylmethylideneamino)cyclohexyl]methanimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以16.9 g的产率得到(1R,2R)-N1,N2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Synthesis, structure and photoluminescence properties of naphthalene-based chiral zinc(II) complexes

  摘要：

  Two novel chiral zinc(II) complexes containing naphthalene moieties, namely [Zn(CMN)Cl-2] (1) and [Zn (CBN)Cl-2] (2), were obtained through the reaction of zinc(II) chloride with, respectively, (1R,2R)-N-1-(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (CMN) and (1R,2R)-N-1,N-2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (CBN) in ethanol. The ligands CMN and CBN were characterized via infrared, nuclear magnetic resonance and absorption spectroscopic analyses. As regards to the two complexes, a comprehensive single crystal X-ray diffraction investigation showed that in both cases the zinc (II) ion is surrounded by two N atoms of CMN/CBN and two chloro groups, and has a distorted tetrahedral structure, though 2 also contains an additional naphthalene group. The photo-physical properties of 1 and 2 were examined based on their electronic absorption and photoluminescence spectra. Both complexes exhibited ultraviolet emissions (both at 335 nm in CHCl3; 336 and 385 nm for 1 and 337 nm for 2 in their solid states) under 278-298 nm excitation. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2020.114643
• 作为试剂：
  描述：

  乙醛酸乙酯 、 (1-phenylvinyl)carbamic acid benzyl ester 在 (1R,2R)-N1,N2-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到
  参考文献：
  名称：

  METHOD OF ENANTIOSELECTIVE NUCLEOPHILIC ADDITION REACTION OF AN ENAMIDE TO A GLYOXYLIC ACID ESTER

  摘要：

  公开号：

  EP1707556B1

文献信息

• Nickel-Catalyzed Asymmetric <i>C</i>-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides
  作者：Vijayarajan Devannah、Rajgopal Sharma、Donald A. Watson

  DOI：10.1021/jacs.9b04175

  日期：2019.5.29

  A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched

  描述了使用镍催化对硝基烷烃进行不对称 C-烷基化的一般催化方法。该方法能够使用与各种官能团兼容的温和反应条件，从容易获得的 α-溴酰胺形成高度对映体富集的 β-硝基酰胺。当与后续反应相结合时，该方法允许获得具有含氮完全取代的碳中心的高度对映体富集的产品。
• Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine
  作者：Nicolas Duguet、Adele Donaldson、Stuart M. Leckie、James Douglas、Peter Shapland、Thomas B. Brown、Gwydion Churchill、Alexandra M.Z. Slawin、Andrew D. Smith

  DOI：10.1016/j.tetasy.2010.03.001

  日期：2010.3

  The synthesis of a range of C-2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction. (C) 2010 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.