(S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(2-(bis(ethylthio)methyl)piperidin-1-yl)methanone | 1263193-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(2-(bis(ethylthio)methyl)piperidin-1-yl)methanone
• 英文别名: [(2S)-2-[bis(ethylsulfanyl)methyl]piperidin-1-yl]-(5-methoxy-2-nitro-4-phenylmethoxyphenyl)methanone
• CAS: 1263193-94-7
• 化学式: C₂₅H₃₂N₂O₅S₂
• 分子量: 504.671
• InChiKey: MORRQMIIOOZRCN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(2-(bis(ethylthio)methyl)piperidin-1-yl)methanone 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies

  摘要：

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.030
• 作为产物：
  描述：

  2-硝基-4-苄氧基-5-甲氧基苯甲酸 、 (2S)-piperidine-2-carboxaldehyde diethyl dithioacetal 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(2-(bis(ethylthio)methyl)piperidin-1-yl)methanone
  参考文献：
  名称：

  Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies

  摘要：

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.030

文献信息

• Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies
  作者：Nagula Markandeya、Nagula Shankaraiah、Ch. Sanjeeva Reddy、Leonardo Silva Santos、Ahmed Kamal

  DOI：10.1016/j.tetasy.2010.10.030

  日期：2010.11

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved