adamantan-2-ylacetonitrile | 38121-87-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: adamantan-2-ylacetonitrile
• 英文别名: 2-adamantylacetonitrile；adamant-2-yl acetonitrile；2-Adamantyl-essigsaeurenitril；2-Adamantylacetonitril；2-(2-adamantyl)acetonitrile
• CAS: 38121-87-8
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: VMOQPWKALNDRAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  adamantan-2-ylacetonitrile 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 64.5h， 生成 (+/-)-1-(adamantan-2-yl)-2-propanamine
  参考文献：
  名称：

  Mariani; Schenone; Bondavalli, Farmaco, Edizione Scientifica, 1980, vol. 35, # 5, p. 430 - 440

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Adamantyl-cyanessigsaeure 在 铜 作用下， 生成 adamantan-2-ylacetonitrile
  参考文献：
  名称：

  Landa,S. et al., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 1445 - 1449

  摘要：

  DOI：

文献信息

• Methods and compositions for treating amyloid-related diseases
  申请人：Kong Xianqi

  公开号：US20060223855A1

  公开（公告）日：2006-10-05

  Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.

  描述了用于治疗或预防与淀粉样蛋白相关疾病的方法、化合物、药物组合物和试剂盒。
• Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann-Löffler Manifold
  作者：Estefanía Del Castillo、Mario D. Martínez、Alexandra E. Bosnidou、Thomas Duhamel、Calvin Q. O'Broin、Hongwei Zhang、Eduardo C. Escudero-Adán、Marta Martínez-Belmonte、Kilian Muñiz

  DOI：10.1002/chem.201804504

  日期：2018.11.22

  position‐selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann‐Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5‐ and 1,6‐hydrogen‐atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation

  介绍了一种创新的脂族烃键位置选择性多卤化方法。该反应在Hofmann-Löffler流形中进行，酰胺基是唯一的介体，诱导选择性1,5-和1,6--氢原子转移，然后进行卤化。完成了多达四个固有CH键功能化的多次卤化事件。对于总共27个不同的实例（包括混合卤代），证明了这种新进入多卤代反应的广泛适用性以及由此产生的合成可能性。
• Thiazole cardiovascular agents
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04064258A1

  公开（公告）日：1977-12-20

  1-Alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene-N-alkyloxazolid ine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dines and derivatives are also intermediates for the 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s. The 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s can be prepared by base or acid hydrolysis of the corresponding 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative; or by treatment of the corresponding 3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine. Similarly the 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative can be prepared from the corresponding 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s via treatment with an aldehyde or ketone.

  1-烷基氨基-3-(5-环烷基氨基甲酰硫唑-2-氧基)-2-丙醇；5-(5-环烷基氨基甲酰硫唑-2-氧甲基-N-烷氧杂环丙烷和/或其2-取代的噁唑烷衍生物，以及制备这种化合物的方法。这些化合物表现出心血管活性，并且在治疗哺乳动物的心脏异常病症方面很有用。这些化合物也在治疗哺乳动物的高血压方面很有用。5-(5-环烷基氨基甲酰硫唑-2-氧甲基)-N-烷氧杂环丙烷和衍生物也是1-烷基氨基-3-(5-环烷基氨基甲酰硫唑-2-氧基)-2-丙醇的中间体。1-烷基氨基-3-(5-环烷基氨基甲酰硫唑-2-氧基)-2-丙醇可以通过对应的5-(5-环烷基氨基甲酰硫唑-2-氧甲基)-N-烷氧杂环丙烷或衍生物的碱或酸水解来制备；或者通过将对应的3-(5-环烷基氨基甲酰硫唑-2-氧基)-2,3-环氧丙烷与所需的烷基胺处理而制备。类似地，5-(5-环烷基氨基甲酰硫唑-2-氧甲基)-N-烷氧杂环丙烷或衍生物可以通过与醛或酮处理来制备，后者来自相应的1-烷基氨基-3-(5-环烷基氨基甲酰硫唑-2-氧基)-2-丙醇。
• 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。
• ADAMANTANE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：EP1731504A1

  公开（公告）日：2006-12-13

  Provided are an adamantane derivative characterized by having a structure represented by Formula (I) and a process for producing an adamantane derivative in which n is 0 in Formula (I) described above, wherein an adamantane compound is reacted with a nitrile compound and then with acid halide or acid anhydride of (meth)acrylic acids. The adamantane derivative characterized by having a structure represented by Formula (I) is a novel adamantane derivative which is useful as a monomer for functional resins such as a photosensitive resin in the photolithograpy field, and it can efficiently be produced by the production process described above.

  本发明提供了一种金刚烷衍生物，其特征在于具有由式（I）表示的结构，并提供了一种生产上述式（I）中 n 为 0 的金刚烷衍生物的工艺，其中金刚烷化合物与腈化合物反应，然后与（甲基）丙烯酸的酸卤化物或酸酐反应。金刚烷衍生物的结构如式（I）所示，是一种新型金刚烷衍生物，可用作光刻领域中光敏树脂等功能性树脂的单体，并可通过上述生产工艺高效生产。