2-(adamantane-2-ylidene)propionitrile | 1431612-16-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(adamantane-2-ylidene)propionitrile
• 英文别名: 2-(adamant-2-ylidene)propionitrile
• CAS: 1431612-16-6
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: HOBYVTSXVMBBIT-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(adamantane-2-ylidene)propionitrile 在 sodium tetrahydroborate 、 氢气 、 nickel dichloride 作用下， 以 异丙醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以79%的产率得到2-(2-adamantyl)-propionitrile
  参考文献：
  名称：

  Colloid and nanosized catalysts in organic synthesis: XII. Hydrogenation of carbonitriles catalyzed by nickel nanoparticles

  摘要：

  Hydrogenation of carbonitriles catalyzed by nickel nanoparticles in isopropanol proceeds under atmospheric pressure of hydrogen within 6-15 h to yield mainly secondary amines. Hydrogenation of alpha-aminonitriles results in reductive decyanation. beta-Aminonitriles undergo hydrogenolysis at the nitrogen-carbon bond.

  DOI：

  10.1134/s1070363216020110
• 作为产物：
  描述：

  金刚烷酮 、 丙腈 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到2-(adamantane-2-ylidene)propionitrile
  参考文献：
  名称：

  金刚烷酮与亚甲基活性化合物的缩合

  摘要：

  开发了一种方便的方法来制备具有2-金刚烷基自由基的潜在生物活性物质以及用于其合成的中间体。进行金刚烷酮与亚甲基活性化合物的缩合反应，并确定了反应特征。

  DOI：

  10.1134/s1070427213030191

文献信息

• Reduction of unsaturated adamantyl-containing nitriles with lithium aluminum hydride in 2-methyltetrahydrofuran
  作者：I. A. Novakov、B. S. Orlinson、N. N. Mamutova、E. N. Savel’ev、E. A. Potayonkova、L. A. Pyntya、M. A. Nakhod

  DOI：10.1134/s1070363216060062

  日期：2016.6

  Reduction of unsaturated adamantyl-containing nitriles with lithium aluminum hydride in 2-methyltetrahydrofuran was examined. It was found that under the synthesis conditions a simultaneous reduction of the double bond and the nitrile group successfully occurred. The presence of bulky substituents in the α-position to the adamantyl moiety of nitriles led to a significant increase in the synthesis duration

  研究了在2-甲基四氢呋喃中用氢化铝锂还原不饱和含金刚烷基的腈。发现在合成条件下，双键和腈基同时还原成功。在腈的金刚烷基部分的α位上存在大量取代基导致合成持续时间的显着增加。仅通过提高温度并使用两倍过量的氢化锂铝才能获得令人满意的目标化合物收率。
• Synthesis of 2-adamantyl-containing amines as compounds with potential pharmacological activity
  作者：I. A. Novakov、B. S. Orlinson、E. N. Savel’ev、E. A. Alykova、A. M. Pichugin、M. A. Kovaleva、A. O. Sergeev、N. A. Demidovich、E. V. Kondrat’ev

  DOI：10.1007/s11172-022-3701-1

  日期：2022.12

  The regularities of the reduction of unsaturated nitriles containing the 2-adamantyl fragment with lithium aluminum hydride and nickel—aluminum alloy were studied. In both cases, the double bond and nitrile group were simultaneously reduced. The presence of bulky substituents in the substrate in the α-position to the adamantyl fragment and hydroxy groups significantly retards the process, and the 80–90% yield of the corresponding products is achieved only when the temperature is raised to 65 °C. In the case of using a nickel—aluminum alloy, its 4—6-fold excess is required. The calculation of the potential pharmacological activity of the synthesized compounds shows that they can have antiviral, analgesic, and antidiabetic activity.

  研究了用氢化锂铝和镍铝合金还原含有 2-金刚烷基片段的不饱和腈的规律性。在这两种情况下，双键和腈基同时被还原。底物中金刚烷基片段和羟基的 α 位上存在笨重的取代基会大大延缓这一过程，只有当温度升至 65 ℃ 时，相应产物的产率才能达到 80-90%。如果使用镍铝合金，则需要过量 4-6 倍。对合成化合物潜在药理活性的计算表明，它们具有抗病毒、镇痛和抗糖尿病活性。
• Reduction of unsaturated adamantane-containing nitriles
  作者：I. A. Novakov、B. S. Orlinson、N. N. Mamutova、E. N. Saveliev、E. A. Potaenkova

  DOI：10.1134/s107036321507004x

  日期：2015.7

  The regularities of reduction of adamantane-containing unsaturated nitriles with Raney nickel were studied. It was shown that in the reaction conditions simultaneous reduction of both the double bond and the nitrile group occurs. The reduction of 2-(5-hydroxyadamant-2-ylidene)alkyl nitriles requires a longer time.