2-N-piperidino-2-cyanoadamantane | 81498-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-N-piperidino-2-cyanoadamantane
• 英文别名: 2-Piperidin-1-yladamantane-2-carbonitrile
• CAS: 81498-31-9
• 化学式: C₁₆H₂₄N₂
• 分子量: 244.38
• InChiKey: VLDKLTUXICYDAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-N-piperidino-2-cyanoadamantane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到2-Piperidino-adamantan
  参考文献：
  名称：

  Reductive decyanation of 2-(dialkylamino)adamantane-2-carbonitriles

  摘要：

  DOI：

  10.1134/s1070428014070215
• 作为产物：
  描述：

  金刚烷酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-N-piperidino-2-cyanoadamantane
  参考文献：
  名称：

  Synthesis of 2-amino-2-cyanoadamantane and its derivatives

  摘要：

  Synthetic routes to new amino nitriles with the functional groups at the 2-position of the adamantane core, based on reactions of adamantanonimines with acetone cyanohydrin or of adamantanone cyanohydrin with aliphatic amines, are considered. The products can be used for preparing new biologically active substances, unsymmetrical adamantyl-containing diamines or amino acids.

  DOI：

  10.1134/s1070427212090145

文献信息

• Reactions of 2-(N,N-dialkyl)amino-2-adamantylcarbonitriles with Grignard reagents
  作者：N. A. Tankabekyan、Yu. V. Popov、V. M. Mokhov

  DOI：10.1134/s1070363213100277

  日期：2013.10

  General procedure of the synthesis of 2-alkyl-2(N,N-dialkyl)aminoadamantanes (IIa–IId). To the Grignard reagent prepared from 0.025 mol of magnesium and 0.018 mol of an alkyl halide in 15–20 mL of tetrahydrofuran was added a solution of 0.009 mol of aminonitrile I in 10 mL of tetrahydrofuran. The mixture was heated at 40°C with stirring for 4 h, then cooled and mixed with 0.5 g of water. After separating

  合成 2-烷基-2(N,N-二烷基)氨基金刚烷 (IIa-IId) 的一般程序。将 0.009 摩尔氨基腈 I 在 10 毫升四氢呋喃中的溶液添加到由 0.025 摩尔镁和 0.018 摩尔卤代烷在 15-20 毫升四氢呋喃中制备的格氏试剂中。将混合物在搅拌下在40°C加热4小时，然后冷却并与0.5g水混合。分离固相后，蒸发滤液。目标产物在真空中蒸馏。2-甲基-2-(N-哌啶子基)金刚烷(IIa)。产率 75%，bp 171–172°C (20 mm Hg)，nD 1.5312。Н NMR 光谱, δ, ppm (J, Hz): 1.19–1.84 m (14Н, 金刚烷; 6H, 哌啶, 0.86 s (3Н, СН3), 2.20 d [2Н, N(CH2), J 14.5], 2.78 d [2Н, N(CH2), J 13.7]. 质谱 (EI, 70 eV), m/e (Irel
• Synthesis and biological activity of phencyclidine and its adamantylamine derivatives
  作者：A Ferle-Vidović、M Kaštelan、D Petrović、L Šuman、M Kaselj、D Škare、K Mlinarić-Majerski

  DOI：10.1016/0223-5234(93)90140-a

  日期：1993.1

  1-(2-Phenyl-2-adamantyl)amines 2a-c were synthesized and their biological activity evaluated by in vitro testing of their effects on the proliferative and reproductive ability of a human tumor cell strain and nonmalignant mouse and hamster fibroblasts in culture, and these effects compared with those of phencyclidine 1. Experiments with asynchronously growing cell populations revealed inhibition of proliferation in both normal and malignant cell strains in the presence of 10(-5) M 1 and of morpholine derivative 2c. However, there were no changes in growth rate in the presence of the 2 adamantyl derivatives 2a and 2b. Reduction of survival in both normal and malignant cell strains was also observed, but at higher concentrations and with less toxic side effects of 2a and 2b. Combined effects of the adamantyl derivatives 2a-c and ionizing irradiation were also studied by determination of cell survival. No radiation-modifying effect was observed. Investigation of these compounds in mice showed significantly less toxicity and enhanced anesthetic effect of the adamantyl derivatives 2a-b than of phencyclidine itself.
• Fotadar, Upinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 11, p. 1006 - 1007
  作者：Fotadar, Upinder

  DOI：——

  日期：——
• Mlinaric-Majerski, Kata; Kaselj, Mira; Skare, Danko, Organic Preparations and Procedures International, 1992, vol. 24, # 5, p. 501 - 508
  作者：Mlinaric-Majerski, Kata、Kaselj, Mira、Skare, Danko

  DOI：——

  日期：——
• FOTADAR, UPINDER, INDIAN J. CHEM., 1981, 20, N 11, 1006-1007
  作者：FOTADAR, UPINDER

  DOI：——

  日期：——