5-cyclohexylpentanenitrile | 5962-90-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-cyclohexylpentanenitrile
• 英文别名: 5-cyclohexyl-valeronitrile；5-Cyclohexyl-valeronitril；Cyclohexanepentanenitrile
• CAS: 5962-90-3
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: GBVKMZARVUQOAF-UHFFFAOYSA-N

物化性质

• 沸点：
  141-143 °C(Press: 18 Torr)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-cyclohexylpentanenitrile 在 三(2-氯乙基)胺 作用下， 生成 5-(4-cyclohexyl-butyl)-tetrazole
  参考文献：
  名称：

  THE REACTION OF NITRILES WITH HYDRAZOIC ACID: SYNTHESIS OF MONOSUBSTITUTED TETRAZOLES

  摘要：

  DOI：

  10.1021/jo01151a027
• 作为产物：
  描述：

  5-cyclohexyl-valeric acid amide 在 sodium metabisulfite 、 三氯氧磷 作用下， 生成 5-cyclohexylpentanenitrile
  参考文献：
  名称：

  Ketimines. III. ι-Cyclohexylalkyl Alkyl Type¹

  摘要：

  DOI：

  10.1021/ja01145a016

文献信息

• Electrochemical Cyanation of Alcohols Enabled by an Iodide-Mediated Phosphine P(V/III) Redox Couple
  作者：Xuewen Guo、Nathan G. Price、Qilei Zhu

  DOI：10.1021/acs.orglett.4c02550

  日期：2024.9.6

  We report herein a mild electrochemical method to transform alcohols into their corresponding nitriles by using commercially available reagents. This protocol accepts substrates with various functional groups including those that are susceptible to oxidative decomposition. Mechanistic studies revealed a critical iodide-mediated phosphine electrochemical oxidation pathway leading to the alkoxyphosphonium

  我们在此报告了一种温和的电化学方法，通过使用市售试剂将醇转化为相应的腈。该方案接受具有各种官能团的底物，包括那些易于氧化分解的底物。机理研究揭示了一个关键的碘化物介导的膦电化学氧化途径，产生烷氧基鏻中间体，然后被氰化物亲核试剂进行亲核取代。该方法演示了电化学在醇底物的直接亲核取代和同系化中替代偶氮型试剂的用途。
• TRICYCLIC PYRROLOPYRIDINE COMPOUND, AND JAK INHIBITOR
  申请人：Nissan Chemical Corporation

  公开号：EP2955181B1

  公开（公告）日：2019-10-30
• Nickel-Catalyzed Cross-Coupling between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides
  作者：Anne Eeg Jensen、Paul Knochel

  DOI：10.1021/jo0105787

  日期：2002.1.1

  In the presence of Bu4NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu4NI. The bicyclic secondary diorganozinc 6 prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.
• 2-Substituted histamines with G-protein-stimulatory activity
  作者：H Detert、A Hagelüken、R Seifert、W Schunack

  DOI：10.1016/0223-5234(96)88235-3

  日期：1995.1

  The cationic-amphiphilic 2-substituted histamines, 2-(3-chlorophenyl)histamine (2-[2-(3-chlorophenyl)-1H-imidazol-4-yl]ethanamine) and 2-(2-cyclohexylethyl)histamine, activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) of the G(i)-subfamily by a receptor-independent mechanism. We studied structure-activity relationships of 2-substituted histamine derivatives for this G-protein activation using six known and 12 newly synthesized compounds. Elongation of the alkyl chain between imidazole and the ring system enhanced the potency and efficiency of substances in activating high-affinity GTP hydrolysis, ie the enzymatic activity of G-protein alpha-subunits, in membranes of HL-60 leukemic cells. Cyclopentyl-, cyclohexyl- and norbornyl-substituted histamines were more effective and potent than phenyl-substituted histamines in mediating G-protein activation in HL-60 membranes and in activating reconstituted bovine brain G(i)/G(o)-proteins. Our data show that the chain length and the type of ring system are important determinants for receptor-independent G-protein activation by 2-substituted histamines. With respect to histamine H-1-receptors, most of the substances studied displayed weak antagonistic activity.