(6S)-1,6-dibenzylpiperazine-2,3,5-trione | 253188-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6S)-1,6-dibenzylpiperazine-2,3,5-trione
• CAS: 253188-22-6
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: MDGSELSGJFFBEB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴乙酸甲酯 、 (6S)-1,6-dibenzylpiperazine-2,3,5-trione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到methyl 2-[(3S)-3,4-dibenzyl-2,5,6-trioxopiperazin-1-yl]acetate
  参考文献：
  名称：

  Piperazine-2,3,5-triones in the synthesis of constrained peptides

  摘要：

  Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N-4, bis-alkylated at N-4 and C-6, or tris-alkylated at N-4, N-1, and C-6 under mild basic conditions; this provides access to i) alpha,alpha-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(alpha)-N bond formation; iii) DKP analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01602-0
• 作为产物：
  描述：

  L-苯丙氨酰胺 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 生成 (6S)-1,6-dibenzylpiperazine-2,3,5-trione
  参考文献：
  名称：

  Piperazine-2,3,5-triones in the synthesis of constrained peptides

  摘要：

  Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N-4, bis-alkylated at N-4 and C-6, or tris-alkylated at N-4, N-1, and C-6 under mild basic conditions; this provides access to i) alpha,alpha-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(alpha)-N bond formation; iii) DKP analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01602-0

文献信息

• Piperazine-2,3,5-triones in the synthesis of constrained peptides
  作者：Patrick D. Bailey、Andrew N. Boa、S.Richard Baker、Joanne Clayson、Ernest J. Murray、Georgina M. Rosair

  DOI：10.1016/s0040-4039(99)01602-0

  日期：1999.10

  Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N-4, bis-alkylated at N-4 and C-6, or tris-alkylated at N-4, N-1, and C-6 under mild basic conditions; this provides access to i) alpha,alpha-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(alpha)-N bond formation; iii) DKP analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.