[(2S,5R)-5-(4-Benzyloxycarbonylamino-butyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester | 499775-08-5

• 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: [(2S,5R)-5-(4-Benzyloxycarbonylamino-butyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester
• CAS: 499775-08-5
• 化学式: C₂₅H₂₉N₃O₆
• 分子量: 467.522
• InChiKey: WSYOKECEMIYDAN-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(2S,5R)-5-(4-Benzyloxycarbonylamino-butyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester 在 palladium oxide on charcoal 甲酸 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 以51%的产率得到2-[(2S,5R)-5-(4-aminobutyl)-3,6-dioxopiperazin-2-yl]acetic acid
  参考文献：
  名称：

  Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines

  摘要：

  Twenty-four bifunctional diketopiperazines, cyclo(-Aax-Bbx-) consisting of glutamic or aspartic acid (Aax) and lysine, ornithine or diaminobutyric (Dab) acid (Bbx) were synthesized. D-Dab moiety was incorporated as D-Gln followed by Hoffman-type rearrangement induced by Phl[OC(O)CF3](2.) Cyclization conditions for the related linear dipeptide precursors allowing racemization to be kept at a minimum were determined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01021-9
• 作为产物：
  描述：

  N2-[叔丁氧羰基]-N6-[苄氧羰基]-D-赖氨酸 在 N-甲基吗啉 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 、 仲丁醇 为溶剂， 反应 20.0h， 生成 [(2S,5R)-5-(4-Benzyloxycarbonylamino-butyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester
  参考文献：
  名称：

  Cyclic dipeptides as building blocks for combinatorial libraries. Part 2: Synthesis of bifunctional diketopiperazines

  摘要：

  Twenty-four bifunctional diketopiperazines, cyclo(-Aax-Bbx-) consisting of glutamic or aspartic acid (Aax) and lysine, ornithine or diaminobutyric (Dab) acid (Bbx) were synthesized. D-Dab moiety was incorporated as D-Gln followed by Hoffman-type rearrangement induced by Phl[OC(O)CF3](2.) Cyclization conditions for the related linear dipeptide precursors allowing racemization to be kept at a minimum were determined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01021-9