1,4-dibenzyl-3-(3'-hydroxypropyl)piperazine-2,5-dione | 117872-44-3

• 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: 1,4-dibenzyl-3-(3'-hydroxypropyl)piperazine-2,5-dione
• 英文别名: 1,4-Dibenzyl-3-(3-hydroxypropyl)piperazine-2,5-dione
• CAS: 117872-44-3
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: LQRQYBLMALPPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dibenzyl-3-(3'-hydroxypropyl)piperazine-2,5-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 以46%的产率得到rac-7,9-dibenzyl-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione
  参考文献：
  名称：

  Studies on asymmetric synthesis of bicyclomycin precursors. A chemoenzymatic route to chiral 2,5-diketopiperazines and 2-oxa-bicyclo[4.2.2]decane-8,10-diones

  摘要：

  A novel asymmetric route to bicyclomycin analogues, 2-oxa-bicyclo[4.2.2]decane-8,10-diones, is described. The key chiral synthons 3-(omega-hydroxyalkyl)-2,5-diketopiperazines 3a-c were obtained via enzymatic kinetic resolution of their respective acetates 2a-c using hydrolases (up to >98% ee, E > 200). The chiral 2,5-diketopiperazines were then transformed into their bicyclic derivatives in a stereospecific manner. Circular dichroism and NMR studies were performed to determine the absolute and relative configuration of the obtained products. The biocatalytic approach gave high stereoselectivities in comparison to the chiral pool synthesis from glutamic acid (58% ee) and thus demonstrated the ability of hydrolases to discriminate a remote stereocenter. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.004
• 作为产物：
  描述：

  N,N'-dibenzylpiperazine-2,5-dione 在 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.5h， 生成 1,4-dibenzyl-3-(3'-hydroxypropyl)piperazine-2,5-dione
  参考文献：
  名称：

  Dawson, Ian M.; Gregory, Julian A.; Herbert, Richard B., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2585 - 2594

  摘要：

  DOI：

文献信息

• Studies towards the synthesis of bicyclomycin precursors: Synthesis of<i>N,N</i>′-disubstituted 2,5-diketopiperazines in solution and on solid phase
  作者：Anna Fryszkowska、Ryszard Ostaszewski

  DOI：10.1002/jhet.5570450321

  日期：2008.5

  3-(hydroxyalkyl)-N,N′-disubstituted 2,5-diketopiperazine derivatives - compounds required for the bicyclomycin analogues preparation - has been studied. The use of various oxo components in the Ugi multicomponent reaction (U-MCR) has been evaluated. The first example of an semicyclic O,O-acetal employed as an aldehyde equivalent in the U-MCR has been reported. The preparation and the synthetic application of

  已经研究了3-（羟烷基）-N，N′-二取代的2，5-二酮哌嗪衍生物（双环霉素类似物制备所需的化合物）的合成。已评估了在Ugi多组分反应（U-MCR）中使用各种羰基合成物。已经报道了在U-MCR中用作醛当量的半环O，O-缩醛的第一个例子。还描述了在2，5-二酮哌嗪骨架的合成中Wang树脂结合的脂族醛的制备和合成应用。
• DAWSON, IAN M.;GREGORY, JULIAN A.;HERBERT, RICHARD B.;SAMMES, PETER G., J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2585-2593
  作者：DAWSON, IAN M.、GREGORY, JULIAN A.、HERBERT, RICHARD B.、SAMMES, PETER G.

  DOI：——

  日期：——
• Dawson, Ian M.; Gregory, Julian A.; Herbert, Richard B., Journal of the Chemical Society. Perkin transactions I, 1988, p. 2585 - 2594
  作者：Dawson, Ian M.、Gregory, Julian A.、Herbert, Richard B.、Sammes, Peter G.

  DOI：——

  日期：——
• Studies on asymmetric synthesis of bicyclomycin precursors. A chemoenzymatic route to chiral 2,5-diketopiperazines and 2-oxa-bicyclo[4.2.2]decane-8,10-diones
  作者：Anna Fryszkowska、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2017.08.004

  日期：2017.9

  A novel asymmetric route to bicyclomycin analogues, 2-oxa-bicyclo[4.2.2]decane-8,10-diones, is described. The key chiral synthons 3-(omega-hydroxyalkyl)-2,5-diketopiperazines 3a-c were obtained via enzymatic kinetic resolution of their respective acetates 2a-c using hydrolases (up to >98% ee, E > 200). The chiral 2,5-diketopiperazines were then transformed into their bicyclic derivatives in a stereospecific manner. Circular dichroism and NMR studies were performed to determine the absolute and relative configuration of the obtained products. The biocatalytic approach gave high stereoselectivities in comparison to the chiral pool synthesis from glutamic acid (58% ee) and thus demonstrated the ability of hydrolases to discriminate a remote stereocenter. (C) 2017 Elsevier Ltd. All rights reserved.