8(S)-tert-Butyloxycarbonylamino-3-oxo-8a(R)-indolizidine | 134936-00-8

• 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: 8(S)-tert-Butyloxycarbonylamino-3-oxo-8a(R)-indolizidine
• 英文别名: tert-butyl N-[(8S,8aR)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizin-8-yl]carbamate
• CAS: 134936-00-8
• 化学式: C₁₃H₂₂N₂O₃
• 分子量: 254.329
• InChiKey: DOJZIVXJDBRKLX-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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 sodium hydroxide 、 氢气 、 sodium iodide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 17.25h， 生成 8(S)-tert-Butyloxycarbonylamino-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

文献信息

• A facile synthesis of 8-amino-3-oxoindolizidine derivatives as conformationally restricted ornithyl pseudodipeptides
  作者：I. Gómez-Monterrey、M.J. Domínguez、R. González-Muñiz、J.R. Harto、M.T. García-López

  DOI：10.1016/s0040-4039(00)74495-9

  日期：1991.2

  One pot procedure for the synthesis of 8-amino-3-oxoindolizidines from Z-delta-protected ornithyl ketomethylene pseudodipeptide derivatives is described. This procedure, involving hydrogenolysis of the Z-group, intramolecular reductive amination and gamma-lactamization, provides readily access to a variety of 3-oxoindolizidines of defined stereochemistry at C-8 and C-8a.