(8S,8aR,2R)-2-Benzyl-8(S)-tert-butyloxycarbonylamino-2-methoxycarbonyl-3-oxoindolizidine | 136890-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (8S,8aR,2R)-2-Benzyl-8(S)-tert-butyloxycarbonylamino-2-methoxycarbonyl-3-oxoindolizidine
• 英文别名: methyl (2R,8S,8aR)-2-benzyl-8-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-1,5,6,7,8,8a-hexahydroindolizine-2-carboxylate
• CAS: 136890-94-3
• 化学式: C₂₂H₃₀N₂O₅
• 分子量: 402.491
• InChiKey: DVRVLRXKBCUSLU-GSHUGGBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8S,8aR,2R)-2-Benzyl-8(S)-tert-butyloxycarbonylamino-2-methoxycarbonyl-3-oxoindolizidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到8(S)-Amino-2(R)-benzyl-2-methoxycarbonyl-3-oxo-8a(R)-indolizidine
  参考文献：
  名称：

  Synthesis of 2-substituted 8-amino-3-oxoindolizidine-2-carboxylic acid derivatives as peptide conformation mimetics

  摘要：

  The synthesis of methyl 8-tert-butyloxycarbonylamino-3-oxoindolizidine-2-carboxylate and its alkyl derivatives bearing Phe, Trp and Asp side chains at C2 position are described. These bridged bicyclic lactams, obtained with high and moderate stereocontrol at C-8a and C2, respectively, have appropriate N- and C-protecting groups making them suitable for incorporation as spacers into higher peptides.

  DOI：

  10.1016/s0040-4020(01)90127-9
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-苄氧羰基-L-鸟氨酸 在 palladium on activated charcoal 氢气 、 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 1.25h， 生成 (8S,8aR,2R)-2-Benzyl-8(S)-tert-butyloxycarbonylamino-2-methoxycarbonyl-3-oxoindolizidine
  参考文献：
  名称：

  Synthesis of 2-substituted 8-amino-3-oxoindolizidine-2-carboxylic acid derivatives as peptide conformation mimetics

  摘要：

  The synthesis of methyl 8-tert-butyloxycarbonylamino-3-oxoindolizidine-2-carboxylate and its alkyl derivatives bearing Phe, Trp and Asp side chains at C2 position are described. These bridged bicyclic lactams, obtained with high and moderate stereocontrol at C-8a and C2, respectively, have appropriate N- and C-protecting groups making them suitable for incorporation as spacers into higher peptides.

  DOI：

  10.1016/s0040-4020(01)90127-9

文献信息

• CCK-4 restricted analogues containing a 3-oxoindolizidine skeleton
  作者：Rosario González-Muñiz、MaJosé Domínguez、Mercedes Martín-Martínez、Rosario Herranz、MaTeresa García-López、Ana Barber、Santiago Ballaz、Joaquín Del Río

  DOI：10.1016/0960-894x(96)00160-6

  日期：1996.4

  A series of CCK-4 restricted analogues, incorporating a 3-oxoindolizidine bicyclic lactam as conformational constraint, is described. The 8-(Boc-tryptophyl)amino-2-benzyl derivatives behave as weak CCK-A or CCK-B receptor antagonists. The main factors for selectivity are the configuration at C-2 position of the 3-oxoindolizidine ring and at the Trp residue. Copyright (C) 1996 Elsevier Science Ltd