1-aminoethyl-3-(4'-aminophenyl)adamantane | 180268-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-aminoethyl-3-(4'-aminophenyl)adamantane
• 英文别名: 4-[3-(2-aminoethyl)adamantan-1-yl]aniline；4-[3-(2-aminoethyl)-1-adamantyl]aniline
• CAS: 180268-71-7
• 化学式: C₁₈H₂₆N₂
• 分子量: 270.418
• InChiKey: LYLDOJZYZORJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-氯喹啉 、 1-aminoethyl-3-(4'-aminophenyl)adamantane 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以37%的产率得到N-(4-{3-[2-(quinolin-4-ylamino)ethyl]adamantan-1-yl}phenyl)quinolin-4-amine
  参考文献：
  名称：

  Arylation of adamantanamines: V. Palladium-catalyzed amination of isomeric chloroquinolines with diamines of the adamantane series

  摘要：

  Palladium-catalyzed arylation of diamines of the adamantane series with isomeric 2-, 4-, and 6-chloroquinoline was studied, and optimal conditions for the synthesis of the corresponding N,N'-diaryl derivatives were found. N,N-Diarylation products of primary amino groups in the diamines bearing 2-aminoethyl and 4-aminophenyl substituents were readily formed.

  DOI：

  10.1134/s1070428012120019
• 作为产物：
  描述：

  N-<2-(1-Adamantyl)-aethyl>-acetamid 在 盐酸 、 水 、 硝酸 作用下， 以 硫酸 为溶剂， 反应 14.5h， 生成 1-aminoethyl-3-(4'-aminophenyl)adamantane
  参考文献：
  名称：

  金刚烷系列二胺的合成和精神活性

  摘要：

  金刚烷和其他多环烃的各种氨基衍生物除了具有显着的抗病毒作用 [I, 2] 外，还具有许多有价值的精神药理学特性。例如，这些化合物可用作抗抑郁药，也可在临床实践中用作抗帕金森病药物 [3]。这些化合物的精神活性谱由氨基取代基的性质、它们在多环核中的位置以及氨基的碱性决定 [4]。为了增加具有多面体结构的潜在精神药物制剂的种类，我们研究了与 1,3-二氨基金刚烷 (I) [5] 相比，二胺的精神药理学特性在伯氨基与金刚烷核的键合特征方面有所不同。先前描述的 1,3-二（氨基烷基）金刚烷 (I1, 如[6]中所述，通过推导相应的金刚烷羧酸二酰胺来合成IIl)。含苯基的二胺（IV、V）是通过N-乙酰氨基烷基金刚烷与乙酰苯胺在浓硫酸介质中在65%硝酸作为氧化剂存在下缩合，然后水解得到的：

  DOI：

  10.1007/bf02218874

文献信息

• Synthesis of Macrobicycles Comprising 2,7-Diaminonaphthalene Moiety via Palladium-Catalyzed Amination Reaction
  作者：Irina P. Beletskaya、Alexei N. Uglov、Georgii A. Zubrienko、Anton S. Abel、Alexei D. Averin、Olga A. Maloshitskaya、Alla Bessmertnykh-Lemeune、Franck Denat

  DOI：10.3987/com-13-s(s)87

  日期：——

  An original synthetic approach to bismacrocyclic ligands bearing naphthalene moiety was developed. First, the macrocycles comprising 2,7diaminonaphthalene fragment were reacted with 2,7-dibromonaphthalene, 4,4'dibromobiphenyl or bromobenzyl bromide affording corresponding NN'bis(bromoaryl) or N,N'-bis(bromobenzyl) substituted macrocycles. Pd-catalyzed macrocyclization of these compounds with a wide range of di- and polyamines led to a series of new macrobicyclic ligands. The yields of the macrobicycles are strongly dependent on the nature of starting compounds, reaching 35% in some cases.
• Arylation of adamantanamines: VI. Palladium-catalyzed arylation of amines and diamines of the adamantane series with 3-bromopyridine
  作者：A. D. Averin、T. Yu. Baranova、A. S. Abel、V. V. Kovalev、A. K. Buryak、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428013010016

  日期：2013.1

  Palladium-catalyzed amination of 3-bromopyridine with amines of the adamantane series in the presence of Pd(dba)(2)/L [L = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl or 2-dimethylamino-2'-dicyclohexylphosphinobiphenyl] gave the desired N-(pyridin-3-yl)-substituted amines in 74-97% yields. Diamines of the adamantane series reacted with 2 equiv of 3-bromopyridine in a complicated fashion to produce mono- and triaryl-substituted derivatives as by-products, while the yields of N,N'-diarylation products were 18-56%. DOI: 10.1134/S1070428013010016
• ——
  作者：Yu. V. Popov、T. K. Korchagina、G. V. Chicherina、T. A. Ermakova

  DOI：10.1023/a:1016321823035

  日期：——

  New Schiff bases containing both adamantyl and phenyl fragments in a single molecule were synthesized by condensation of appropriate diamines with aromatic aldehydes. The condensation products were brought into reduction and nucleophilic addition reactions.
• Synthesis and psychotropic activty of diamines from the adamantane series
  作者：I. A. Novakov、V. I. Petrov、B. S. Orlinson、I. A. Grigor'ev、A. A. Ozerov、O. A. Kuznechikov

  DOI：10.1007/bf02218874

  日期：1996.2

  bonding of the primary amino group to adamantane nucleus in comparison with 1,3-diaminoadamantane (I) [5]. The previously described 1,3-di(aminoalkyl)adamantanes (I1, lIl) were synthesized by deduction of the corresponding diamides of adamantanecarboxylic acids as described in [6]. The phenyl-containing diamines (IV, V) were obtained by condensation of N-acetylaminoaikyladamantanes with acetanilide in a

  金刚烷和其他多环烃的各种氨基衍生物除了具有显着的抗病毒作用 [I, 2] 外，还具有许多有价值的精神药理学特性。例如，这些化合物可用作抗抑郁药，也可在临床实践中用作抗帕金森病药物 [3]。这些化合物的精神活性谱由氨基取代基的性质、它们在多环核中的位置以及氨基的碱性决定 [4]。为了增加具有多面体结构的潜在精神药物制剂的种类，我们研究了与 1,3-二氨基金刚烷 (I) [5] 相比，二胺的精神药理学特性在伯氨基与金刚烷核的键合特征方面有所不同。先前描述的 1,3-二（氨基烷基）金刚烷 (I1, 如[6]中所述，通过推导相应的金刚烷羧酸二酰胺来合成IIl)。含苯基的二胺（IV、V）是通过N-乙酰氨基烷基金刚烷与乙酰苯胺在浓硫酸介质中在65%硝酸作为氧化剂存在下缩合，然后水解得到的：
• Arylation of adamantanamines: V. Palladium-catalyzed amination of isomeric chloroquinolines with diamines of the adamantane series
  作者：O. K. Grigorova、A. D. Averin、A. S. Abel、O. A. Maloshitskaya、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1134/s1070428012120019

  日期：2012.12

  Palladium-catalyzed arylation of diamines of the adamantane series with isomeric 2-, 4-, and 6-chloroquinoline was studied, and optimal conditions for the synthesis of the corresponding N,N'-diaryl derivatives were found. N,N-Diarylation products of primary amino groups in the diamines bearing 2-aminoethyl and 4-aminophenyl substituents were readily formed.