N-甲基-1-金刚烷胺 | 3717-39-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-甲基-1-金刚烷胺
• 中文别名: 1-金刚烷胺,N-甲基-,盐酸盐
• 英文名称: (1-adamantyl)(methyl)amine hydrochloride
• 英文别名: N-methyladamantan-1-amine hydrochloride；1-methylaminoadamantane hydrochloride；N-methyladamantyl-1-amine hydrochloride；Adamantan-1-methylmin-hydrochlorid；N-methyladamantan-1-amine;hydrochloride
• CAS: 3717-39-3
• 化学式: C₁₁H₁₉N*ClH
• 分子量: 201.739
• InChiKey: MGWTWRYRZDCDBG-UHFFFAOYSA-N

物化性质

• 熔点：
  250-251 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2921300090

反应信息

• 作为反应物：
  描述：

  N-甲基-1-金刚烷胺 在 氯化亚砜 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 <1>Adamantyl-<2-chlor-ethyl>-methyl-amin
  参考文献：
  名称：

  抗病毒药。2.与1-金刚烷胺有关的化合物的构效关系。

  摘要：

  DOI：

  10.1021/jm00288a019
• 作为产物：
  描述：

  N-(1-金刚烷)甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以95%的产率得到N-甲基-1-金刚烷胺
  参考文献：
  名称：

  Substituted 1-phenyl-2-cyclopropylmethylamines with high affinity and selectivity for sigma sites

  摘要：

  A series of 1-phenyl-2-cyclopropylmethylamines structurally related to (+)- and (-)-MPCB were synthesized and their binding affinities for or, oz, opioid and dopamine (D-2) receptors were evaluated. Substitution of the cis-N-normetazocine with different aminic moieties provided compounds with high affinity and selectivity for sigma binding sites with respect to opioid and dopamine (D2) receptors. The observed increase in sigma(2) affinity as compared to the parent(+)-MPCB, supports the idea that the particular stereochemistry of (+)-cis-N-normetazocine affects sigma(1) selectivity but does not affect ol affinity. The (+/-)-cis isomers of methyl 2-[(1-adamantylamino)methyl]-1-phenylcyclopropane-1-carboxylate (18) displayed a higher affinity and selectivity for the ol and sigma(2) receptor subtypes compared to the (+/-)-trans 19. interestingly, the enantiomer (-)-cis 18 displayed a preference for ol receptor subtype whereas the (+)-cis 18 did for sigma(2). These results prompt us to synthesize compounds with modification of nitrogen and carboxyl groups. The compounds obtained showed high affinities and selectivity for sigma sites. Moreover, modifications of carboxyl groups provided compounds with the highest affinities in the series. In particular, compound 25 with reverse-type ester showed a K-i of 0.6 and 4.05 nM for sigma(1) and sigma(2) binding sites, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00072-9

文献信息

• Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources
  作者：Kaushik Chakrabarti、Anju Mishra、Dibyajyoti Panja、Bhaskar Paul、Sabuj Kundu

  DOI：10.1039/c8gc00863a

  日期：——

  A Ru(II) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The

  报道了使用甲醇作为甲基化剂，由有机叠氮化物介导的Ru（II）络合物介导的各种N，N-二甲基和N-单甲基胺的合成。该方法已成功应用于溴化物衍生物和叠氮化钠在甲醇中的一锅法反应。明显地，通过控制反应时间，几个N-单甲基化和N，N选择性合成-二甲基化胺。通过与不同有机叠氮化物的制备规模反应以及抗眩晕药倍他司汀的合成，揭示了该串联过程的实际适用性。进行了一些动力学实验和DFT研究，以了解这种转化的机理。
• Heteroaryl Amide Derivatives
  申请人：Hutchison Alan J.

  公开号：US20100216763A1

  公开（公告）日：2010-08-26

  Heteroaryl amide derivatives are provided, of the Formula: wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the treatment of conditions associated with pathological receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using such compounds to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.

  提供了杂环酰胺衍生物，其化学式为：其中变量如本文所述。这些化合物是配体，可用于体内或体外调节特定受体活性，并且在治疗与人类、家畜伴侣动物和家畜动物的病理性受体激活相关的疾病方面特别有用。提供了用于治疗此类疾病的制药组合物和方法，以及用于受体定位研究的此类配体的方法。
• Heteroaryl amide derivatives
  申请人：H. Lundbeck A/S

  公开号：US20130172549A1

  公开（公告）日：2013-07-04

  Heteroaryl amide derivatives are provided, of the Formula: wherein variables are as described herein. Such compounds are ligands that may be used to modulate specific receptor activity in vivo or in vitro, and are particularly useful in the treatment of conditions associated with pathological receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using such compounds to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.

  本发明提供了杂环酰胺衍生物，其化学式为：其中变量如此处所述。这些化合物是配体，可用于调节体内或体外特定受体的活性，并且特别适用于治疗与人类、家畜伴侣动物和家畜动物中的病理性受体激活相关的疾病。本发明还提供了用于治疗此类疾病的药物组合物和方法，以及用于受体定位研究的配体使用方法。
• ——
  作者：N. V. Makarova、E. I. Boreko、I. K. Moiseev、N. I. Pavlova、M. N. Zemtsova、S. N. Nikolaeva、G. V. Vladyko

  DOI：10.1023/a:1014086507352

  日期：——
• ——
  作者：N. V. Makarova、I. K. Moiseev、M. N. Zemtsova

  DOI：10.1023/a:1020486424505

  日期：——

  4-(1-Adamantyl)-1-aminobutan-3-one hydrochlorides were synthesized by the Mannich reaction of (1-adamantyl)acetone with paraformaldehyde and secondary amine hydrochlorides (diethylamine, dibenzylamine, piperidine). Analogous reactions of I-adamantyl(methyl)amine with acetone, p-hydroxyacetophenone, and methyl 2-thienyl ketone gave 1-[(1-adamantyl)methylamino]propan-3-one hydrochlorides.