(2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyryl chloride | 319926-22-2

• 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: (2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyryl chloride
• 英文别名: (2S,3R)-3-(cyclopentylmethyl)-4-oxo-4-piperidin-1-yl-2-[(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl]butanoyl chloride
• CAS: 319926-22-2
• 化学式: C₂₂H₃₄ClN₃O₄
• 分子量: 439.983
• InChiKey: OKCDAAZEEPBCFH-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyryl chloride 在 甲醇 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4S,5R,6S)-6-[(2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2
• 作为产物：
  描述：

  1-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl]piperidine 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 以100%的产率得到(2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyryl chloride
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2