N¹⁵-bis-Boc cyclo-[Gly-(L)-Val] | 1010079-68-1

• 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: N¹⁵-bis-Boc cyclo-[Gly-(L)-Val]
• 英文别名: ditert-butyl (3S)-2,5-dioxo-3-propan-2-yl-(115N)1,4-diazinane-1,4-dicarboxylate
• CAS: 1010079-68-1
• 化学式: C₁₇H₂₈N₂O₆
• 分子量: 357.412
• InChiKey: UZHHXFJVADRFDO-RAGBWZAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N¹⁵-bis-Boc cyclo-[Gly-(L)-Val] 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到tert-butyl (2S)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino]-5-oxo-2-propan-2-yl-2H-pyrrole-1-carboxylate
  参考文献：
  名称：

  [15N]-Isotopic labeling: a suitable tool to study the reactivity of bis lactams

  摘要：

  The unexpected reactivity of 2,5-diketopiperazines under basic conditions, thanks to N-Boc activation, allows access to valuable pharmacological scaffolds, such as original statine derivatives. Toward this transannular rearrangement of activated lactams (TRAL), we report here the study of his lactam reactivity using [(15)N]-isotopic labeling. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.159
• 作为产物：
  描述：

  (3S)-3-propan-2-yl-(115N)1,4-diazinane-2,5-dione 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以78%的产率得到N¹⁵-bis-Boc cyclo-[Gly-(L)-Val]
  参考文献：
  名称：

  [15N]-Isotopic labeling: a suitable tool to study the reactivity of bis lactams

  摘要：

  The unexpected reactivity of 2,5-diketopiperazines under basic conditions, thanks to N-Boc activation, allows access to valuable pharmacological scaffolds, such as original statine derivatives. Toward this transannular rearrangement of activated lactams (TRAL), we report here the study of his lactam reactivity using [(15)N]-isotopic labeling. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.159

文献信息

• From Diketopiperazines to Hydantoins: An Unprecedented Rearrangement
  作者：Isabelle Parrot、Guilhem Chaubet、Guillaume Cazals、Aurélien Lebrun、Jean Martinez

  DOI：10.1055/s-0033-1340622

  日期：——

  Bis-Boc-activated 2,5-diketopiperazines on reaction with potassium hydroxide or sodium methoxide in dry tetrahydrofuran led to Boc-protected hydantoins through an unprecedented ring contraction. This rearrangement was applied to several monosubstituted 2,5-diketopiperazines with good yields and regioselectivity.
• [15N]-Isotopic labeling: a suitable tool to study the reactivity of bis lactams
  作者：Thibault Coursindel、Daniel Farran、Jean Martinez、Georges Dewynter

  DOI：10.1016/j.tetlet.2007.11.159

  日期：2008.1

  The unexpected reactivity of 2,5-diketopiperazines under basic conditions, thanks to N-Boc activation, allows access to valuable pharmacological scaffolds, such as original statine derivatives. Toward this transannular rearrangement of activated lactams (TRAL), we report here the study of his lactam reactivity using [(15)N]-isotopic labeling. (C) 2007 Elsevier Ltd. All rights reserved.