trans-N-phenyl-1,2-cyclohexanediamine | 96185-44-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: trans-N-phenyl-1,2-cyclohexanediamine
• 英文别名: N-(trans-2-Aminocyclohexyl)anilin；N-phenylcyclohexane-1,2-diamine；N-phenyl-trans-cyclohexane-1,2-diyldiamine；N-Phenyl-trans-cyclohexan-1,2-diyldiamin；(1S,2S)-2-N-phenylcyclohexane-1,2-diamine
• CAS: 96185-44-3；100316-59-4
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: UWISRGCDRULEQO-RYUDHWBXSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  328.0±35.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-N-phenyl-1,2-cyclohexanediamine 、 丙烯腈 以 甲醇 为溶剂， 反应 19.0h， 以99%的产率得到trans-N-phenyl-N'-(2-cyanoethyl)-1,2-cyclohexanediamine
  参考文献：
  名称：

  Molecular Scaffolds. 2. Intramolecular Hydrogen Bonding in 1,2-Diaminoethane Diureas

  摘要：

  Intramolecular hydrogen bonding creates remarkably stable folded structures in diurea derivatives of substituted 1,2-diaminoethanes. 1,2-Diaminoethane diureas 2 [PhN(CONHR(1))CH2CH2N(CONHR(2))CH2CH2CN; 2a, R(1) = R(2) = Ph; 2b, R(1) = (S)-CH(CH(2)Ph)CO2CH3, R(2) = (S)-CH(i-Pr)CO2CH3; 2c, R(1) = R(2) = (S)-CH(CH(2)Ph)CO2CH3; 2d, R(1) = R(2) = CH3] are prepared in high yield by reaction of diamine 4 (PhNHCH(2)CH(2)NHCH(2)CH(2)CN) with isocyanates. The differing reactivities of the two amino groups in 4 permit the preparation of diureas bearing different substituents R(1) and R(2) (e.g., 2b) with greater than or equal to 95% regioselectivity. The N-phenyl substituent on the 1,2-diamine backbone of diureas 2 helps maintain conformational homogeneity by controlling the direction of the urea group that bears this substituent (NCONHR(1)). Intramolecular hydrogen bonding aligns the other urea group (NCONHR(2)). Infrared and H-1 NMR spectroscopic studies indicate ureas 2 are largely or wholly hydrogen bonded (ca. 75-100%) in chloroform solution, whereas the homologous 1,3-diaminopropane diureas 1 [PhN(CONHR(1))CH2CH2CH2N(CONHR(2))CH2CH2CN] exhibit a lesser degree of intramolecular hydrogen bonding (25-80%). These findings indicate that the 9-membered hydrogen-bonded ring structures of 1,2-diaminoethane diureas 2 are more stable than the 10-membered hydrogen-bonded ring structures;of 1,3-diaminopropane diureas 1. H-1 NMR and X-ray crystallographic studies establish that the 1,2-diaminoethane backbone of diureas 2 adopts an anti conformation, both in solution and in the solid state.

  DOI：

  10.1021/ja00106a011
• 作为产物：
  描述：

  N-(7-azabicyclo<4.1.0>hept-7-yl)phthalimide 在 镍 高氯酸 、 二氮烯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 trans-N-phenyl-1,2-cyclohexanediamine
  参考文献：
  名称：

  β-Funktionalisierte肼N -Phthalimidoaziridinen和ihre氢解N，N-Spaltung zu Aminen

  摘要：

  N-邻苯二甲酰亚胺基叠氮烷中的β-官能肼及其氢解N，N裂解成胺

  DOI：

  10.1002/hlca.19850680128

文献信息

• An efficient and recyclable chitosan supported copper(II) heterogeneous catalyst for C–N cross coupling between aryl halides and aliphatic diamines
  作者：Chandan Bodhak、Ashis Kundu、Animesh Pramanik

  DOI：10.1016/j.tetlet.2014.11.120

  日期：2015.1

  convenient methodology has been developed for synthesis of mono N-arylated aliphatic 1,2- and 1,3-diamines and amino alcohols. A highly efficient and renewable heterogeneous chitosan supported copper(II) catalyst has been employed for the C–N cross coupling between aryl halides and aliphatic diamines/amino alcohols. The main advantages of this reaction are the high yields of the products, reduced reaction

  已经开发了一种有用且方便的方法来合成单N-芳基化的脂肪族1,2-和1,3-二胺和氨基醇。一种高效且可再生的多聚壳聚糖负载铜（II）催化剂已用于芳基卤化物与脂肪族二胺/氨基醇之间的C–N交叉偶联。该反应的主要优点是产物的高产率，缩短的反应时间，方便的后处理步骤，催化剂的可更新性以及产物的金属污染少。所有这些因素使目前的C–N交叉偶联反应经济，绿色和可持续。
• Asymmetric meso-aziridine ring-opening reactions using a chiral zirconium catalyst
  作者：Kazutaka Seki、Rongmin Yu、Yumi Yamazaki、Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1039/b914271c

  日期：——

  A chiral zirconium catalyst prepared from Zr(OtBu)4 and a chiral tridentate BINOL was found to be effective for asymmetric meso-aziridine ring-opening reactions with aniline derivatives. The N-benzhydryl group on the product obtained was easily cleaved to give the corresponding amine in high yield under reductive conditions.

  研究发现，由 Zr(OtBu)4 和手性三叉 BINOL 制备的手性锆催化剂对苯胺衍生物的不对称间氮丙啶开环反应非常有效。在还原条件下，所得产物上的 N-二苯甲基基团很容易裂解，从而得到高产率的相应胺。
• Chemokine receptor binding heterocyclic compounds
  申请人：——

  公开号：US20040220207A1

  公开（公告）日：2004-11-04

  Novel compounds that are useful for targeting chemokine receptors are disclosed. These compounds are complex tertiary amines.

  本发明揭示了用于靶向趋化因子受体的新化合物。这些化合物是复杂的三级胺。
• Production of 1.2-diaminocyclohexanes
  申请人：BASF AG

  公开号：US02828313A1

  公开（公告）日：1958-03-25
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS
  申请人：ANORMED INC.

  公开号：EP1317445B1

  公开（公告）日：2009-03-11