(4S,7R,8R,8aS)-2-benzyl-8-(2-hydroxyethyl)-7-(1-hydroxy-1-methylethyl)-4-phenyloctahydropyrrolo[1,2-a]pyrazin-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (4S,7R,8R,8aS)-2-benzyl-8-(2-hydroxyethyl)-7-(1-hydroxy-1-methylethyl)-4-phenyloctahydropyrrolo[1,2-a]pyrazin-1-one
• 英文别名: (4S,7R,8R,8aS)-2-benzyl-8-(2-hydroxyethyl)-7-(2-hydroxypropan-2-yl)-4-phenyl-3,4,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-1-one
• 化学式: C₂₅H₃₂N₂O₃
• 分子量: 408.541
• InChiKey: RWBVJPCJHIAEJM-ACESQOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  64
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,7R,8R,8aS)-2-benzyl-8-(2-hydroxyethyl)-7-(1-hydroxy-1-methylethyl)-4-phenyloctahydropyrrolo[1,2-a]pyrazin-1-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以54%的产率得到(2S,3R,4R)-3-(2-Hydroxy-ethyl)-4-(1-hydroxy-1-methyl-ethyl)-pyrrolidine-2-carboxylic acid benzyl-phenethyl-amide
  参考文献：
  名称：

  A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines

  摘要：

  The intramolecular 1,3-dipolar cycloaddition of homochiral dihydroimidazolium ylides, generated in situ, is the key reaction in a sequence that rapidly affords optically active 2,3,4-trisubstituted pyrrolidines suitably functionalised for further elaboration. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00111-1
• 作为产物：
  描述：

  (4S,7R,8R,8aS)-2-benzyl-7-ethoxycarbonyl-8-(2-hydroxyethyl)-4-phenyloctahydropyrrolo[1,2-a]pyrazin-1-one 在 异丙苯 、 甲基锂 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到(4S,7R,8R,8aS)-2-benzyl-8-(2-hydroxyethyl)-7-(1-hydroxy-1-methylethyl)-4-phenyloctahydropyrrolo[1,2-a]pyrazin-1-one
  参考文献：
  名称：

  A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines

  摘要：

  The intramolecular 1,3-dipolar cycloaddition of homochiral dihydroimidazolium ylides, generated in situ, is the key reaction in a sequence that rapidly affords optically active 2,3,4-trisubstituted pyrrolidines suitably functionalised for further elaboration. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00111-1

文献信息

• An enantioselective route to pyrrolidines: removal of the chiral template from homochiral pyrroloimidazoles
  作者：Raymond C.F. Jones、Kevin J. Howard、John S. Snaith、Alexander J. Blake、Wang-Shei Li、Peter J. Steel

  DOI：10.1016/j.tet.2011.08.099

  日期：2011.11

  Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines

  从旋光的吡咯并咪唑类化合物中进行两步还原性去除，可以从均手性的4，5-二氢咪唑鎓内酯的1，3-偶极环加成中获得旋光性的取代的吡咯烷。取代基的选择性操纵提供了例如天然存在的和其他光学活性的脯氨酸衍生物，以及光学活性的吡咯烷核苷和吲哚并核苷。
• A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines
  作者：Raymond C.F. Jones、Kevin J Howard、John S Snaith

  DOI：10.1016/s0040-4039(97)00111-1

  日期：1997.3

  The intramolecular 1,3-dipolar cycloaddition of homochiral dihydroimidazolium ylides, generated in situ, is the key reaction in a sequence that rapidly affords optically active 2,3,4-trisubstituted pyrrolidines suitably functionalised for further elaboration. (C) 1997 Elsevier Science Ltd.