1r,3c-Dimethyl-2t-nitrocyclohexan | 51607-12-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1r,3c-Dimethyl-2t-nitrocyclohexan
• CAS: 51607-12-6
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: IBXUPOMAMWZDSE-JIGDXULJSA-N

物化性质

• 沸点：
  222.3±7.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3r.5c-Dimethyl-4t-nitrocyclohexen-(1) 生成 1r,3c-Dimethyl-2t-nitrocyclohexan
  参考文献：
  名称：

  在Δ双键的反应性：不饱和化合物-III的立体化学和反应3 0cyclohexene和Δ 4个相对于它们的构象-octalin衍生物

  摘要：

  在Δ的双键的反应性的研究3个与该环中的侧链和Me的取代基一个极性取代基环己烯衍生物已经表明，对于这些化合物的优选构象，它们的立体化学的indepenent，具有极性基团的轴向，从而产生环上相互作用。这种相互作用降低了环双键的亲核性。Δ的类似研究4 -octalin -1,2-二羧酸和它们的酯已经表明，在对比的是报道构象分配3个的优选构象，即使对于反式衍生物是那些在diaxial位置的极性subtituents。

  DOI：

  10.1016/0040-4020(67)85137-8

文献信息

• Synthesis and Pharmacological Evaluation of 5-Pyrrolidinylquinoxalines as a Novel Class of Peripherally Restricted κ-Opioid Receptor Agonists
  作者：Christian Bourgeois、Elena Werfel、Fabian Galla、Kirstin Lehmkuhl、Héctor Torres-Gómez、Dirk Schepmann、Babette Kögel、Thomas Christoph、Wolfgang Straßburger、Werner Englberger、Michael Soeberdt、Sabine Hüwel、Hans-Joachim Galla、Bernhard Wünsch

  DOI：10.1021/jm500940q

  日期：2014.8.14

  5-Pyrrolidinyl substituted perhydroquinoxalines were designed as conformationally restricted κ-opioid receptor agonists restricted to the periphery. The additional N atom of the quinoxaline system located outside the ethylenediamine κ pharmacophore allows the fine-tuning of the pharmacodynamic and pharmacokinetic properties. The perhydroquinoxalines were synthesized stereoselectively using the concept of late stage diversification of the central building blocks 14. In addition to high κ-opioid receptor affinity they demonstrate high selectivity over μ, δ, σ1, σ2, and NMDA receptors. In the [35S]GTPγS assay full agonism was observed. Because of their high polarity, the secondary amines 14a (log D7.4=0.26) and 14b (log D7.4=0.21) did not penetrate an artificial blood-brain barrier. 14b was able to inhibit the spontaneous pain reaction after rectal mustard oil application to mice (ED50=2.35 mg/kg). This analgesic effect is attributed to activation of peripherally located κ receptors, since 14b did not affect centrally mediated referred allodynia and hyperalgesia.