(R,R)-N1,N2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine | 1115639-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R,R)-N1,N2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine
• 英文别名: (R,R)-N¹,N²-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine；(1R,2R)-N,N'-dimethyl-N,N'-bis((1-naphthyl)methyl)cyclohexane-1,2-diamine
• CAS: 1115639-94-5
• 化学式: C₃₀H₃₄N₂
• 分子量: 422.613
• InChiKey: LBSAFGJZDASUEO-LOYHVIPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 (R,R)-N1,N2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Rapid and controlled polymerization of rac-lactide using copper(II) complexes of methyl-naphthalenylmethyl-(R,R)-1,2-diaminocyclohexanes

  摘要：

  Novel enantiopure Cu(II) complexes of (R,R)-N-1,N-2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine (1-NMCD) and (R,R)-N-1,N-2-dimethyl-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (2-NMCD) ligands were synthesized and characterized by X-ray diffraction. X-ray diffraction analysis revealed that the molecular structures of the synthesized complexes were mononuclear with Cu(II) atoms in distorted square planar geometries. The diisopropoxide derivatives generated in situ catalyzed ring opening polymerization (MP) of rac-lactide (rac-LA) in a controlled fashion and displayed unusually high activities (10 s or 25 s for complete conversion). Heterotactic enriched PLA (with P-r up to 0.90) was obtained with initiator bearing 2-NMCD in CH2Cl2. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2015.03.003
• 作为产物：
  描述：

  (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 1-萘甲醛 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 36.5h， 以34%的产率得到(R,R)-N1,N2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral liquid crystals

  摘要：

  Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen-lithium exchange. Bis-aryl compounds I and 2, 2,3-dibromonorbornadiene 3, and 1,2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen-lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. Enantioselectivities in the range of 20-35% ee have been detected for this new type of asymmetric synthesis. The prochiral compounds 3 and 4 were also dissolved in a chiral liquid crystal based on organic solutions of poly-gamma-benzyl-L-glutamate and analyzed using natural abundance deuterium 2D NMR spectroscopy. The spectroscopic discrimination of enantiotopic sites in these solutes has been observed and discussed from the point of view of orientational order. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.003

文献信息

• Two aspects of the desymmetrization of selected prochiral aromatic or vinylic dihalides: enantioselective halogen–lithium exchange and prochiral recognition in chiral liquid crystals
  作者：Chun-An Fan、Benoît Ferber、Henri B. Kagan、Olivier Lafon、Philippe Lesot

  DOI：10.1016/j.tetasy.2008.12.003

  日期：2008.12

  Several classes of prochiral dihalides have been identified as potential candidates for asymmetric halogen-lithium exchange. Bis-aryl compounds I and 2, 2,3-dibromonorbornadiene 3, and 1,2-diiodoferrocene 4 were prepared and used as substrates in the asymmetric halogen-lithium exchange reaction. The enantioselective mono-lithiation was achieved in good yields by various combinations of n-BuLi and chiral ligands. Enantioselectivities in the range of 20-35% ee have been detected for this new type of asymmetric synthesis. The prochiral compounds 3 and 4 were also dissolved in a chiral liquid crystal based on organic solutions of poly-gamma-benzyl-L-glutamate and analyzed using natural abundance deuterium 2D NMR spectroscopy. The spectroscopic discrimination of enantiotopic sites in these solutes has been observed and discussed from the point of view of orientational order. (C) 2008 Elsevier Ltd. All rights reserved.
• Rapid and controlled polymerization of rac-lactide using copper(II) complexes of methyl-naphthalenylmethyl-(R,R)-1,2-diaminocyclohexanes
  作者：Kyuong Seop Kwon、Jaewon Cho、Saira Nayab、Jong Hwa Jeong

  DOI：10.1016/j.inoche.2015.03.003

  日期：2015.5

  Novel enantiopure Cu(II) complexes of (R,R)-N-1,N-2-dimethyl-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine (1-NMCD) and (R,R)-N-1,N-2-dimethyl-bis(naphthalen-2-ylmethyl)cyclohexane-1,2-diamine (2-NMCD) ligands were synthesized and characterized by X-ray diffraction. X-ray diffraction analysis revealed that the molecular structures of the synthesized complexes were mononuclear with Cu(II) atoms in distorted square planar geometries. The diisopropoxide derivatives generated in situ catalyzed ring opening polymerization (MP) of rac-lactide (rac-LA) in a controlled fashion and displayed unusually high activities (10 s or 25 s for complete conversion). Heterotactic enriched PLA (with P-r up to 0.90) was obtained with initiator bearing 2-NMCD in CH2Cl2. (C) 2015 Elsevier B.V. All rights reserved.