(-)-(S)-2-aminomethyl-1-propylpyrrolidine | 84225-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-(S)-2-aminomethyl-1-propylpyrrolidine
• 英文别名: (S)-N-propyl-2-(aminomethyl)pyrrolidone；[(2S)-1-propylpyrrolidin-2-yl]methanamine
• CAS: 84225-92-3
• 化学式: C₈H₁₈N₂
• mdl: MFCD19205567
• 分子量: 142.244
• InChiKey: TZFATUOLQKYADA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-溴-2,6-二甲氧基苯甲酰氯 、 (-)-(S)-2-aminomethyl-1-propylpyrrolidine 以 氯仿 为溶剂， 反应 0.5h， 以50%的产率得到3-Bromo-2,6-dimethoxy-N-(1-propyl-pyrrolidin-2-ylmethyl)-benzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025
• 作为产物：
  描述：

  1-丙基-L-脯氨酰胺 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以63%的产率得到(-)-(S)-2-aminomethyl-1-propylpyrrolidine
  参考文献：
  名称：

  Hoegberg, Thomas; Raemsby, Sten; Stroem, Peter, Acta Chemica Scandinavica, 1989, vol. 43, # 7, p. 660 - 664

  摘要：

  DOI：

文献信息

• LANNEYE, G. S.;MOERLEIN, S. M.;PARKINSON, D.;WELCH, M. J., J. MED. CHEM., 33,(1990) N, C. 2430-2437
  作者：LANNEYE, G. S.、MOERLEIN, S. M.、PARKINSON, D.、WELCH, M. J.

  DOI：——

  日期：——
• PAULIS, T. DE;KUMAR, YATENDRA;JOHANSSON, L.;RAEMSBY, S.;FLORVALL, L.;HALL+, J. MED. CHEM., 1985, 28, N 9, 1263-1269
  作者：PAULIS, T. DE、KUMAR, YATENDRA、JOHANSSON, L.、RAEMSBY, S.、FLORVALL, L.、HALL+

  DOI：——

  日期：——
• Efficient stereoconservative syntheses of 1-substituted (S)- and (R)-2-aminomethylpyrrolidines and intermediates therein
  申请人：ASTRA LAKEMEDEL AKTIEBOLAG

  公开号：EP0253785B1

  公开（公告）日：1992-11-11
• A STEREOCONSERVATIVE SYNTHESIS OF 1-SUBSTITUTED (S)- AND (R)-2-AMINOMETHYLPYRROLIDINES AND INTERMEDIATES THERETO
  申请人：ASTRA LAKEMEDEL AKTIEBOLAG

  公开号：EP0270596A1

  公开（公告）日：1988-06-15
• US5300660A
  申请人：——

  公开号：US5300660A

  公开（公告）日：1994-04-05