(1R,2R)-N,N′-bis[(5-methylfuran-2-yl)methyl]cyclohexane-1,2-diamine | 1598408-97-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-N,N′-bis[(5-methylfuran-2-yl)methyl]cyclohexane-1,2-diamine
• 英文别名: (R,R)-N¹,N²-bis((5-methylfuran-2-yl)methyl)cyclohexane-1,2-diamine；(1R,2R)-1-N,2-N-bis[(5-methylfuran-2-yl)methyl]cyclohexane-1,2-diamine
• CAS: 1598408-97-9
• 化学式: C₁₈H₂₆N₂O₂
• 分子量: 302.417
• InChiKey: BGZAGKBXGUGDMU-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  50.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N,N′-bis[(5-methylfuran-2-yl)methyl]cyclohexane-1,2-diamine 、 zinc(II) chloride 以 乙醇 为溶剂， 反应 12.0h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis and structural characterisation of zinc complexes bearing furanylmethyl and thiophenylmethyl derivatives of (R,R)-1,2-diaminocyclohexanes for stereoselective polymerisation of poly(rac-lactide)

  摘要：

  Novel dichloro zinc complexes based on enantiopure N,N-diamine ligands bearing furanylmethyl and thiophenylmethyl pendent groups were synthesised, and their crystal structures were determined using X-ray crystallography. The isopropoxide derivatives (generated in situ) of these well-characterised complexes efficiently catalysed the ring-opening polymerisation (ROP) of rac-lactide (rac-LA) at two different temperatures under controlled conditions. Highly heterotactic polylactide (PIA) was obtained with P-r = 0.80 at -25 degrees C in THF. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.055
• 作为产物：
  描述：

  (1R,2R)-N,N′-bis[(5-methylfuran-2-yl)methylidene]cyclohexane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到(1R,2R)-N,N′-bis[(5-methylfuran-2-yl)methyl]cyclohexane-1,2-diamine
  参考文献：
  名称：

  Synthesis and fluorescent properties of novel chiral 1,2-diaminocyclohexane substituted ligands and their complexes

  摘要：

  A series of novel chiral 1,2-diaminocyclohexane derivatives bearing heterocyclic units were synthesized via improved methods under ultrasonic irradiation. The photophysical properties of compounds were studied in ethanol, methanol, and chloroform. The sensitivity of these amines toward Cu2+, Cd2+, and Ni2+ was studied by the UV vis and fluorescent methods. The pi-electron structure of thiophene and bithiophene containing sensors is the most active toward all above mentioned metal ions and is highly selective for Ni2+ and Cd2+. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.092

文献信息

• Synthesis and structural characterisation of copper complexes containing methylthiophene and methylfuryl derivatives of (R,R)-1,2-diaminocyclohexane as precatalysts for polymerisation of rac-lactide
  作者：Ji-Hye Ham、Juhyun Cho、Saira Nayab、Jong Hwa Jeong

  DOI：10.1016/j.ica.2018.04.025

  日期：2018.8

  A series of Cu(II) complexes supported by methylthiophenyl-and methylfuryl-based (R,R)-1,2-diaminocyclohexane frameworks were synthesised. The synthesised complexes were characterised using infrared spectroscopy, elemental analysis, and single-crystal X-ray diffraction studies. The isopropoxide derivatives of the complexes were employed in the ring-opening polymerisation (ROP) of rac-lactide (rac-LA), yielding polylactides with high number-averaged molecular weight. The catalytic species in this study effectively mediated the stereoselective ROP of rac-LA in a physiological manner (P-r up to 0.92 at room temperature), with ROP activity being mainly dependent on steric hindrance and geometric constraints imposed by methyl substituents attached to the methylthiophenyl and methylfuryl ligands. (C) 2018 Elsevier B.V. All rights reserved.
• Copper complexes bearing methylthiophenyl and methylfuranyl derivatives of (R,R)-1,2-diaminocyclohexane: X-ray structures and catalytic exploitation in Henry reaction
  作者：Jaewon Cho、Gang Ho Lee、Saira Nayab、Jong Hwa Jeong

  DOI：10.1016/j.poly.2015.07.023

  日期：2015.10

  Two novel dichloro Cu(II) complexes of (R,R)-N-1,N-2-bis((5-methylthiophen-2-yl)methyl)cyclohexane-1,2-diamine (MTCHD) and (R,R)-N-1,N-2-bis((5-methylfuran-2-yl)methyl)cyclohexane-1,2-diamine (MFCHD) ligands have been synthesised and structurally characterised using X-ray diffraction. The geometry around the Cu(II) centres was distorted square planner. A strong Cu center dot center dot center dot O-furanyl interaction exists in Cu(MFCHD)Cl-2 that leads to the disappearance of original C-2-symmetry of the ligand, resulting in selective R,S-coordination of N atoms in (1R,2R)-1,2-diaminocyclohexane. Catalytic activities of dichloro and diacetato Cu(II) complexes with 3 mol% of iPr(2)NEt were assessed in asymmetric Henry reactions that resulted in moderate to high yields with an enantiomeric excess up to 92%, without air/moisture exclusion. (C) 2015 Elsevier Ltd. All rights reserved.