(trans,trans)-N1,N3-dibenzyl-2-nitrocyclohexane-1,3-diamine | 15910-77-7

• 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: (trans,trans)-N1,N3-dibenzyl-2-nitrocyclohexane-1,3-diamine
• 英文别名: 1r.3c-Bis-benzylamino-2t-nitro-cyclohexan
• CAS: 15910-77-7
• 化学式: C₂₀H₂₅N₃O₂
• 分子量: 339.437
• InChiKey: VZGGZJLQZKZIFK-PMOLBWCYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  505.2±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (trans,trans)-N1,N3-dibenzyl-2-nitrocyclohexane-1,3-diamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 1ref,2trans,3cis-Triamino-cyclohexan-trihydrochlorid
  参考文献：
  名称：

  Lichtenthaler,F.W. et al., Chemische Berichte, 1968, vol. 101, p. 1837 - 1845

  摘要：

  DOI：
• 作为产物：
  描述：

  戊二醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (trans,trans)-N1,N3-dibenzyl-2-nitrocyclohexane-1,3-diamine
  参考文献：
  名称：

  [EN] PERHYDROQUINOXALINE DERIVATIVES USEFUL AS ANALGESICS
  [FR] DÉRIVÉS DE PÉRHYDROQUINOXALINE UTILES EN TANT QU'ANALGÉSIQUES

  摘要：

  本发明涉及按照通式（1）的过氧化喹啉化合物，其作为药物的用途，特别是作为镇痛、止痒和抗炎药剂，以及它们的制备。

  公开号：

  WO2014184355A1

文献信息

• PERHYDROQUINOXALINE DERIVATIVES
  申请人：Wünsch Bernhard

  公开号：US20100311761A1

  公开（公告）日：2010-12-09

  The present invention relates to perhydroquinoxaline derivatives, processes for their preparation, their use for the preparation of a medicament and medicaments containing perhydroquinoxaline derivatives.

  本发明涉及过氢喹喔啉衍生物，其制备方法，其用于制备药物以及含有过氢喹喔啉衍生物的药物。
• Polyamino-Zucker. V. Modellreaktionen zur Aminierung cyclischer Nitrodiole
  作者：Toshio Nakagawa、Tohru Sakakibara、Frieder W. Lichtenthaler

  DOI：10.1246/bcsj.43.3861

  日期：1970.12

  On treatment of lr,3c-diacetoxy-2t-nitrocyclohexane (3) or its 1,3-dimesyloxy analogue 4 with primary amines or ammonia, nitrodiamines (5–11) are obtained via an elimination-addition mechanism. Similar aminations of lr-methyl-1-nitrocyclohexane-2c,6c-diol (15) or its di-O-acetate 16 give C-methyl branched nitrodiamines (12–14), which are also formed by reaction of glutaraldehyde with nitromethane and amines. Structures and conformations of the products obtained were deduced from IR and NMR data.

  在用伯胺或氨、硝基二胺（5-11）处理lr,3c-二乙酰氧基-2t-硝基环己烷（3）或其1,3-二甲基氧基类似物4时，通过消除-加成机制得到硝基二胺（5-11）。lr-甲基-1-硝基环己烷-2c,6c-二醇（15）或其二-O-乙酸酯16的类似胺化反应生成C-甲基支链硝基二胺（12-14），后者也可通过戊二醛与硝基甲烷和胺的反应形成。从红外和核磁共振数据中推断出所得产物的结构和构象。
• Combination of cyclohexane and piperazine based κ-opioid receptor agonists: Synthesis and pharmacological evaluation of trans,trans-configured perhydroquinoxalines
  作者：Christian Bourgeois、Elena Werfel、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.bmc.2014.04.054

  日期：2014.7

  Desymmetrization of the pseudochiral (2r)-configured cyclohexane-1,2,3-triamines 8 with dimethyl oxalate led to racemic aminoquinoxaline-2,3-diones 9. Selective introduction of the kappa pharmacophoric structural elements pyrrolidine and 3,4-dichlorophenylacetamide with a two-carbon distance afforded conformationally restricted kappa agonists 13-15 based on the quinoxaline ring system. In competitive radioligand receptor binding studies the benzylamine 13b, the secondary amine 14b, and the carbamate 15 displayed high kappa receptor affinity. The K-1 value of the lead compound derived methoxycarbonyl derivative 15 is 9.7 nM. However, the x affinity of 15 is exceeded by 13b and 14b with a basic functional group instead of the methoxycarbonyl group in 1-position of the quinoxaline system. The chlorine atoms of the dichlorophenylacetyl residue are essential, since the corresponding phenylacetyl analogs show considerably reduced x affinity. The potent kappa ligands 13b, 14b and 15 are selective over the related mu- and delta-opioid receptors, sigma(1), sigma(2) and NMDA receptors. In the [S-35]GTP gamma S-binding assay 13b behaved as partial agonist with lower activity than U-69,593. (C) 2014 Elsevier Ltd. All rights reserved.