(RS)-1-(adamantan-1-yl)ethane-1,2-diamine | 924911-98-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (RS)-1-(adamantan-1-yl)ethane-1,2-diamine
• 英文别名: 1-(Adamantan-1-yl)ethane-1,2-diamine；1-(1-adamantyl)ethane-1,2-diamine
• CAS: 924911-98-8
• 化学式: C₁₂H₂₂N₂
• 分子量: 194.32
• InChiKey: UKOXMORSBCWDCN-UHFFFAOYSA-N

物化性质

• 沸点：
  299.0±8.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-1-(adamantan-1-yl)ethane-1,2-diamine 在 D-酒石酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (1S)-1-(adamantan-1-yl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis of Chiral Ligands on the Basis of 1-(Adamantan-1-yl)ethane-1,2-diamine

  摘要：

  derivatized diamine was established by X-ray diffraction analysis, and the enantiomeric excess (96%) was determined using HPLC. Diamine and diimine ligands were synthesized on the basis of racemic and chiral (1 S )-1-(adamantan-1-yl)ethane-1,2-diamine. The catalytic activity nickel(II), copper(II), and manganese(II) complexes were studied in model Michael, Henry, and epoxidation reactions.

  DOI：

  10.1134/s1070428021020135
• 作为产物：
  描述：

  (RS)-1-(adamantan-1-yl)ethane-1,2-diaminedihydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.25h， 以90%的产率得到(RS)-1-(adamantan-1-yl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis of Chiral Ligands on the Basis of 1-(Adamantan-1-yl)ethane-1,2-diamine

  摘要：

  derivatized diamine was established by X-ray diffraction analysis, and the enantiomeric excess (96%) was determined using HPLC. Diamine and diimine ligands were synthesized on the basis of racemic and chiral (1 S )-1-(adamantan-1-yl)ethane-1,2-diamine. The catalytic activity nickel(II), copper(II), and manganese(II) complexes were studied in model Michael, Henry, and epoxidation reactions.

  DOI：

  10.1134/s1070428021020135

文献信息

• Synthesis of conformationally constrained adamantane imidazolines with trypanocidal activity
  作者：Ioannis Papanastasiou、Andrew Tsotinis、George B. Foscolos、S. Radhika Prathalingam、John M. Kelly

  DOI：10.1002/jhet.5570450524

  日期：2008.9

  African trypanosomiasis, we report on the synthesis of spiro adamantane 2-imidazolines 8a-f and 9a-c, and their congeneric 5-(1-adamantyl)imidazolines 14 and 15. The potency of these compounds against Trypanosoma brucei was compared to that of rimantadine and found, in the case of compound 14e, to be three fold higher. Together with the other active compounds, 14b and 15b, which were equipotent to rimantadine

  针对开发用于治疗非洲锥虫病的新的金刚烷基砌块的发展，我们报道了螺金刚烷2-咪唑啉8a-f和9a-c以及它们的同类5-（1-金刚烷基）咪唑啉14和15的合成。将这些化合物对布鲁氏锥虫的功效与金刚乙胺的功效进行了比较，发现在化合物14e的情况下，其效力高出三倍。新分子与金刚烷胺等效的其他活性化合物14b和15b一起说明了金刚烷的亲脂性和C1 idine官能团对锥虫杀灭活性的协同作用。
• Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A
  作者：Dimitrios Tataridis、George Fytas、Antonios Kolocouris、Christos Fytas、Nicolas Kolocouris、George B. Foscolos、Elizaveta Padalko、Johan Neyts、Erik De Clercq

  DOI：10.1016/j.bmcl.2006.10.092

  日期：2007.2

  We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and I-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino, heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Chiral Ligands on the Basis of 1-(Adamantan-1-yl)ethane-1,2-diamine
  作者：P. A. Man’kova、A. N. Reznikov、V. A. Shiryaev、M. R. Baimuratov、V. B. Rybakov、Yu. N. Klimochkin

  DOI：10.1134/s1070428021020135

  日期：2021.2

  derivatized diamine was established by X-ray diffraction analysis, and the enantiomeric excess (96%) was determined using HPLC. Diamine and diimine ligands were synthesized on the basis of racemic and chiral (1 S )-1-(adamantan-1-yl)ethane-1,2-diamine. The catalytic activity nickel(II), copper(II), and manganese(II) complexes were studied in model Michael, Henry, and epoxidation reactions.