((R)-1-Methyl-2-phenyl-ethyl)-propyl-amine | 37577-16-5

• 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: ((R)-1-Methyl-2-phenyl-ethyl)-propyl-amine
• 英文别名: Benzeneethanamine, alpha-methyl-N-propyl-, (alphaR)-；(2R)-1-phenyl-N-propylpropan-2-amine
• CAS: 37577-16-5
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: SNPGTHLGFHVIDA-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((R)-1-Methyl-2-phenyl-ethyl)-propyl-amine 生成 N-((R)-1-Methyl-2-phenyl-ethyl)-N-propyl-hydroxylamine
  参考文献：
  名称：

  1-芳基异丙基胺的伯和仲羟胺的旋光异构体的合成路线

  摘要：

  许多光学纯的初级1- arylisopropylamines的通过用相应的benzylimines的氧化转化为3-苯基-2-（1'-arylisopropyl）氧氮环丙烷米氯过苯甲酸。随后3-苯基氧氮丙啶的酸水解产生了光学纯的N-羟基-1-芳基异丙基胺。的作用米氯过苯甲酸对旋光纯的次要1- arylisopropylamines得到光学纯的N-羟基衍生物。通过使用N-三氟乙酰基-1-脯氨酰氯作为试剂的GLC分析羟胺的光学纯度。

  DOI：

  10.1016/0040-4020(75)87006-2
• 作为产物：
  描述：

  对羟基苯乙胺 、 丙醛 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 ((R)-1-Methyl-2-phenyl-ethyl)-propyl-amine
  参考文献：
  名称：

  Identification and exploitation of the .sigma.-opiate pharmacophore

  摘要：

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.

  DOI：

  10.1021/jm00107a033

文献信息

• US5411965A
  申请人：——

  公开号：US5411965A

  公开（公告）日：1995-05-02
• Synthetic routes to optical isomers of primary and secondary hydroxylamines of 1-arylisopropylamines
  作者：A.H. Beckett、K. Haya、G.R. Jones、P.H. Morgan

  DOI：10.1016/0040-4020(75)87006-2

  日期：1975.1

  number of optically pure primary 1-arylisopropylamines were converted to 3-phenyl-2-(1′-arylisopropyl)oxaziridines by the oxidation of the corresponding benzylimines with m-chloroperbenzoic acid. Subsequent acid hydrolysis of the 3-phenyloxaziridines yielded optically pure N-hydroxy-1-arylisopropylamines. The action of m-chloroperbenzoic acid on optically pure secondary 1-arylisopropylamines gave optically

  许多光学纯的初级1- arylisopropylamines的通过用相应的benzylimines的氧化转化为3-苯基-2-（1'-arylisopropyl）氧氮环丙烷米氯过苯甲酸。随后3-苯基氧氮丙啶的酸水解产生了光学纯的N-羟基-1-芳基异丙基胺。的作用米氯过苯甲酸对旋光纯的次要1- arylisopropylamines得到光学纯的N-羟基衍生物。通过使用N-三氟乙酰基-1-脯氨酰氯作为试剂的GLC分析羟胺的光学纯度。
• Identification and exploitation of the .sigma.-opiate pharmacophore
  作者：Richard A. Glennon、J. Doyle Smith、Abd M. Ismaiel、Mahmoud El-Ashmawy、George Battaglia、James B. Fischer

  DOI：10.1021/jm00107a033

  日期：1991.3

  Certain benzomorphan ''sigma-opiates'' such as N-allylnormetazocine (NANM) bind at sigma receptors with modest affinity and with little selectivity (i.e., they also bind at phencyclidine or PCP sites). In order to identify the primary pharmacophore of the benzomorphans, we prepared several amine-substituted derivatives of 1-phenyl-2-aminopropane. Several simple alkyl-substituted analogues were shown to bind at sigma sites with affinities comparable to that of NANM itself; among these was the N-benzyl derivative 9 (K(i) = 117 nM). Lengthening the spacer between the terminal amine and the phenyl group from one to five methylene units resulted in a significant increase in affinity (e.g. 15, K(i) = 6.3 nM). In addition, unlike the benzomorphans, these phenalkylamines do not bind at PCP sites. The results of the present study reveal that (a) the 1-phenyl-2-aminopropane nucleus of the benzomorphans is sufficient for binding at sigma sites provided that the terminal amine is not a primary amine and that (b) introduction of (phenylalkyl)amine substituents affords compounds that represent a new class of high-affinity sigma-selective agents.