(2R,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol | 114677-02-0

• 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: (2R,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol
• 英文别名: [(2R,4S)-4-amino-1-benzylpyrrolidin-2-yl]methanol
• CAS: 114677-02-0
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: JLOPSSDIFIWMDL-NWDGAFQWSA-N

物化性质

• 沸点：
  328.2±32.0 °C(predicted)
• 密度：
  1.119±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯-2-甲氧基-4-甲氨基苯甲酸 、 (2R,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以60%的产率得到(3S,5R)-N-(1-benzyl-5-hydroxymethyl-3-pyrrolidinyl)-5-chloro-2-methoxy-4-methylaminobenzamide
  参考文献：
  名称：

  Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

  摘要：

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.019
• 作为产物：
  描述：

  L-羟基脯氨酸 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium azide 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.5h， 生成 (2R,4S)-(4-amino-1-benzylpyrrolidin-2-yl)methanol
  参考文献：
  名称：

  Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

  摘要：

  Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2(long), D2(short), D3 and D4 as well as 5-HT1(A) and 5-HT2 respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21. the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.019

文献信息

• Access to Optically Active 3-Azido- and 3-Aminopiperidine Derivatives by Enantioselective Ring Expansion of Prolinols
  作者：Anne Cochi、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/ol201769b

  日期：2011.8.19

  The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu4NN3) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a ratio up to 100/0. These 3-azidopiperidines can be reduced to the corresponding 3-aminopiperidines.

  XtalFluor E活化N-烷基脯氨醇可形成叠氮基中间体，该叠氮基中间体可与叠氮化四丁基铵（n Bu 4 NN 3）反应生成3-叠氮基哌啶和/或2-（叠氮甲基）吡咯烷100/0。这些3-叠氮哌啶可以还原为相应的3-氨基哌啶。
• TAKAHATA, HIROKI;TAKAMATSU, TAMOTSU;CHEN, YIN-SHAN;OHKUBO, NAOKI;YAMAZAKI+, J. ORG. CHEM., 55,(1990) N2, C. 3792-3797
  作者：TAKAHATA, HIROKI、TAKAMATSU, TAMOTSU、CHEN, YIN-SHAN、OHKUBO, NAOKI、YAMAZAKI+

  DOI：——

  日期：——