trans-3,6-bis<(phenylmethoxy)methyl>-2,5-piperazinedione | 96843-76-4

• 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: trans-3,6-bis<(phenylmethoxy)methyl>-2,5-piperazinedione
• 英文别名: (3R,6S)-3,6-bis(benzyloxymethyl)piperazine-2,5-dione；cyclo[D-Ser(Bzl)-L-Ser(Bzl)]；trans-3,6-bis[(phenylmethoxy)methyl]-2,5-piperazinedione；(3R,6S)-3,6-bis(phenylmethoxymethyl)piperazine-2,5-dione
• CAS: 96843-76-4
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: DEEJCDRDHJVIGO-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-3,6-bis<(phenylmethoxy)methyl>-2,5-piperazinedione 、 (3R,6R)-3,6-bis(benzyloxymethyl)piperazine-2,5-dione 、 氢化铝锂 生成 (2S,5R)-2,5-bis(phenylmethoxymethyl)piperazine
  参考文献：
  名称：

  NAIR, RAGHUNATHAN V.;WITIAK, DONALD T.

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-O-苄基-D-丝氨酸 、 N-BOC-O-苄基-L-丝氨酸 在 1-羟基苯并三唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 trans-3,6-bis<(phenylmethoxy)methyl>-2,5-piperazinedione
  参考文献：
  名称：

  Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

  摘要：

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].

  DOI：

  10.1080/10610278.2016.1236197

文献信息

• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].
• Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model
  作者：Donald T. Witiak、Raghunathan V. Nair、Franz A. Schmid

  DOI：10.1021/jm00147a018

  日期：1985.9

  Synthesis of trans- and cis-tetrahydrodipyrazino[1,2-a:1',2'-d] pyrazine-1,3,7,9(2H,4H,8H,10H)-tetrone analogues 10 and 11 belonging to the bis(dioxopiperazine) class of antitumor agents and their bis(morpholinomethyl) derivatives 12 and 13 are described with use of 2,5-dimethylpyrazine as the starting material. Synthetic studies utilizing 3,6-disubstituted 2,5-dioxopiperazine precursors are included. Evaluation of 10-13 in the Lewis Lung carcinoma model indicated the bis(morpholinomethyl) analogue cis-13 to be antimetastatic, whereas the trans isomer 12 was toxic at a similar dose effecting a decrease in the life span of treated mice. The parent bis(dioxopiperazines) 10 and 11 were ineffective as antitumor or antimetastatic drugs.
• NAIR, RAGHUNATHAN V.;WITIAK, DONALD T.
  作者：NAIR, RAGHUNATHAN V.、WITIAK, DONALD T.

  DOI：——

  日期：——
• WITIAK, D. T.;NAIR, RAGHUNATHAN, V.;SCHMID, F. A., J. MED. CHEM., 1985, 28, N 9, 1228-1234
  作者：WITIAK, D. T.、NAIR, RAGHUNATHAN, V.、SCHMID, F. A.

  DOI：——

  日期：——
• US4871736A
  申请人：——

  公开号：US4871736A

  公开（公告）日：1989-10-03