(S)-3-dibenzylamino-4-hydroxypyrrol-1-ylbutan-1-one | 676262-43-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-dibenzylamino-4-hydroxypyrrol-1-ylbutan-1-one
• 英文别名: (3S)-3-(Dibenzylamino)-4-hydroxy-1-(1H-pyrrol-1-yl)butan-1-one；(3S)-3-(dibenzylamino)-4-hydroxy-1-pyrrol-1-ylbutan-1-one
• CAS: 676262-43-4
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: OIIYROSPGAHABN-NRFANRHFSA-N

物化性质

• 沸点：
  523.0±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  pyrrole magnesium chloride 、 (S)-(+)-4-dibenzylamino-γ-lactone 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以59%的产率得到(S)-3-dibenzylamino-4-hydroxypyrrol-1-ylbutan-1-one
  参考文献：
  名称：

  Practical ex-chiral-pool methodology for the synthesis of dopaminergic tetrahydroindoles

  摘要：

  Chemo- and regioselective transformations of asparagine gave access to optically active 5- and 6-amino tetrahydroindolizines when the 3-aminobutyrolactone (S)-2 was employed as a key intermediate. The target compounds were approached by a sequential and regiocontrolled bis-electrophilic attack in the positions 2 and 3 of the pyrrole ring system. Receptor binding experiments showed stereocontrolled receptor recognition leading to the D3 selective agonist (S)-8 with D3 binding that is comparable to the natural neurotransmitter dopamine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.041

文献信息

• Practical ex-chiral-pool methodology for the synthesis of dopaminergic tetrahydroindoles
  作者：Markus Bergauer、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.tet.2003.11.041

  日期：2004.1

  Chemo- and regioselective transformations of asparagine gave access to optically active 5- and 6-amino tetrahydroindolizines when the 3-aminobutyrolactone (S)-2 was employed as a key intermediate. The target compounds were approached by a sequential and regiocontrolled bis-electrophilic attack in the positions 2 and 3 of the pyrrole ring system. Receptor binding experiments showed stereocontrolled receptor recognition leading to the D3 selective agonist (S)-8 with D3 binding that is comparable to the natural neurotransmitter dopamine. (C) 2003 Elsevier Ltd. All rights reserved.