(2S,2'S,5S,5'S)-5,5'-dibenzyl-2,2'-bimorpholine | 1208996-03-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,2'S,5S,5'S)-5,5'-dibenzyl-2,2'-bimorpholine
• 英文别名: (2S,5S)-5-benzyl-2-[(2S,5S)-5-benzylmorpholin-2-yl]morpholine
• CAS: 1208996-03-5
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: DBUKRCUJINOQIN-CMOCDZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,2'S,5S,5'S)-5,5'-dibenzyl-2,2'-bimorpholine 、 (R)-3-(hydroxymethyl)cyclopentanone 在 sodium cyanoborohydride 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以15%的产率得到(1R,3S)-(((2S,2S,5S,5S)-5,5-dibenzyl-2,2-bimorpholino)cyclopentyl)methanol
  参考文献：
  名称：

  Synthesis and Biological Activity of Bimorpholine and its Carbanucleoside

  摘要：

  A new enantiomerically pure carbacyclic nucleoside analogue with bimorpholine as a nonaromatic nucleobase was synthesized. The nucleoside analogue and bimorpholine were tested for cytotoxicity using an MTT assay and the xCELLigence System. Both assays revealed that compound 3 was highly cytotoxic at a 50 mu M concentration while the cytotoxic effect of compound 1 was much less prominent. No antiretroviral activity was detected for this compound. In contrast, it acted as a potent inhibitor of hepatitis C virus (HCV) replication. Most likely this effect originates largely from the cytotoxicity of the compound; however, it is possible that a specific mechanism of HCV inhibition also exists.

  DOI：

  10.1080/15257770.2011.621919
• 作为产物：
  描述：

  (2S,2'S,5S,5'S)-4,4',5,5'-tetrabenzyl-2,2'-bimorpholine 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以90%的产率得到(2S,2'S,5S,5'S)-5,5'-dibenzyl-2,2'-bimorpholine
  参考文献：
  名称：

  5,5'-二取代双吗啉的合成

  摘要：

  提出了一种合成 5,5'-二取代双吗啉的通用方法。根据该方法，以酒石酸酯缩醛为原料合成了甲基取代和苄基取代的化合物。目标化合物以良好的收率和高对映体纯度获得。

  DOI：

  10.1080/00397910902964874

文献信息

• Synthesis and Biological Activity of Bimorpholine and its Carbanucleoside
  作者：Kerti Ausmees、Anastasia Selyutina、Kristel Kütt、Kristin Lippur、Tõnis Pehk、Margus Lopp、Eva Žusinaite、Andres Merits、Tõnis Kanger

  DOI：10.1080/15257770.2011.621919

  日期：2011.11

  A new enantiomerically pure carbacyclic nucleoside analogue with bimorpholine as a nonaromatic nucleobase was synthesized. The nucleoside analogue and bimorpholine were tested for cytotoxicity using an MTT assay and the xCELLigence System. Both assays revealed that compound 3 was highly cytotoxic at a 50 mu M concentration while the cytotoxic effect of compound 1 was much less prominent. No antiretroviral activity was detected for this compound. In contrast, it acted as a potent inhibitor of hepatitis C virus (HCV) replication. Most likely this effect originates largely from the cytotoxicity of the compound; however, it is possible that a specific mechanism of HCV inhibition also exists.
• Synthesis of 5,5′-Disubstituted Bimorpholines
  作者：Kristin Lippur、Cindy Elmers、Tiiu Kailas、Aleksander-Mati Müürisepp、Tõnis Pehk、Tõnis Kanger、Margus Lopp

  DOI：10.1080/00397910902964874

  日期：2009.12.30

  A general method for the synthesis of 5,5′-disubstituted bimorpholines is proposed. According to the method, methyl-substituted and benzyl-substituted compounds were synthesized, starting from tartaric ester acetal. Target compounds were obtained in good yield and high enantiomeric purity.

  提出了一种合成 5,5'-二取代双吗啉的通用方法。根据该方法，以酒石酸酯缩醛为原料合成了甲基取代和苄基取代的化合物。目标化合物以良好的收率和高对映体纯度获得。