methyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: VQUKRPXETHQDGX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到methyl (2S)-2-formylpiperidine-1-carboxylate
  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：

  (S,S)-piperidinedicarboxylic acid dimethyl ester 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以10%的产率得到methyl (2S)-2-formylpiperidine-1-carboxylate
  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