(±)-trans-1-benzyloxycarbonyl-3-(diallylamino)-4-hydroxypyrrolidine

• 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: (±)-trans-1-benzyloxycarbonyl-3-(diallylamino)-4-hydroxypyrrolidine
• 英文别名: benzyl (3S,4S)-3-[bis(prop-2-enyl)amino]-4-hydroxypyrrolidine-1-carboxylate
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: RSXDQDHRDQNCPF-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-trans-1-benzyloxycarbonyl-3-(diallylamino)-4-hydroxypyrrolidine 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 144.0h， 生成 (3R,4R)-3-acetoxy-1-(benzyloxycarbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine
  参考文献：
  名称：

  Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines

  摘要：

  Several orthogonally protected racemic trans-3-amino-4-hydroxypyrrolidines have been easily prepared from N-Cbz-3,4-epoxypyrrolidine. Resolution of each racemic compound was accomplished by means of lipase-catalyzed aminolysis, transesterification or hydrolysis reactions. In most cases, the corresponding remaining substrates and the products were obtained with very high enantiomeric excesses. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.112
• 作为产物：
  描述：

  3-CBZ-6-氧杂-3-氮杂二环[3.1.0]己烷 、 二烯丙基胺 以 乙醇 为溶剂， 反应 48.0h， 以80%的产率得到(±)-trans-1-benzyloxycarbonyl-3-(diallylamino)-4-hydroxypyrrolidine
  参考文献：
  名称：

  Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines

  摘要：

  Several orthogonally protected racemic trans-3-amino-4-hydroxypyrrolidines have been easily prepared from N-Cbz-3,4-epoxypyrrolidine. Resolution of each racemic compound was accomplished by means of lipase-catalyzed aminolysis, transesterification or hydrolysis reactions. In most cases, the corresponding remaining substrates and the products were obtained with very high enantiomeric excesses. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.112

文献信息

• Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines
  作者：Jesús A. Rodríguez-Rodríguez、F. Javier Quijada、Rosario Brieva、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/j.tet.2013.04.112

  日期：2013.7

  Several orthogonally protected racemic trans-3-amino-4-hydroxypyrrolidines have been easily prepared from N-Cbz-3,4-epoxypyrrolidine. Resolution of each racemic compound was accomplished by means of lipase-catalyzed aminolysis, transesterification or hydrolysis reactions. In most cases, the corresponding remaining substrates and the products were obtained with very high enantiomeric excesses. (C) 2013 Elsevier Ltd. All rights reserved.