(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(3-trimethylsilyl-2-propynyl)-1H-pyrano[3,4-c]-8-pyridone | 219773-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: (S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(3-trimethylsilyl-2-propynyl)-1H-pyrano[3,4-c]-8-pyridone
• 英文别名: (4S)-4-ethyl-4-hydroxy-6-iodo-7-(3-trimethylsilylprop-2-ynyl)-1H-pyrano[3,4-c]pyridine-3,8-dione
• CAS: 219773-22-5
• 化学式: C₁₆H₂₀INO₄Si
• 分子量: 445.329
• InChiKey: FKDPRNRTZISZRM-INIZCTEOSA-N

物化性质

• 沸点：
  567.7±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(3-trimethylsilyl-2-propynyl)-1H-pyrano[3,4-c]-8-pyridone 在 六甲基二锡 作用下， 生成 7-trimethylsilyl-11-aminocamptothecin
  参考文献：
  名称：

  7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents

  摘要：

  The synthesis and biological evaluation of about one dozen 7-silylcamptothecin derivatives are described. Most new compounds show potencies comparable to or better than camptothecin itself. The best compound, 11-fluoro-10-amino-7-trimethylsilylcamptothecin, is more than 20 times more potent than camptothecin in cell assays. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10181-0
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 (S)-4-乙基-4-羟基-6-碘-3-氧代-1H-吡喃并[3,4-C]-8-吡啶酮 在 sodium hydride 、 lithium bromide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(3-trimethylsilyl-2-propynyl)-1H-pyrano[3,4-c]-8-pyridone
  参考文献：
  名称：

  7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents

  摘要：

  The synthesis and biological evaluation of about one dozen 7-silylcamptothecin derivatives are described. Most new compounds show potencies comparable to or better than camptothecin itself. The best compound, 11-fluoro-10-amino-7-trimethylsilylcamptothecin, is more than 20 times more potent than camptothecin in cell assays. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10181-0

文献信息

• Cascade 4+1 Radical Annulations of 2,6-Disubstituted Phenyl Isonitriles with <i>N</i>-Propargyl-6-Iodopyridones: Scope, Mechanism and Regioselective Synthesis of 7,9-Disubstituted Camptothecin Analogs
  作者：Dennis Curran、Wu Du

  DOI：10.1055/s-2003-40327

  日期：——

  The reaction of o,o′-dialkyl-substituted aryl isonitriles with N-propargyl-6-iodopyridones provides 11H-indolizino[1,2-b]quinolin-9-ones with significant regioselectivity in favor of the more crowded product. The usefulness of the method is illustrated with a regioselective synthesis of (20S)-7-trimethylsilyl-9-isopropyl camptothecin.

  o,o'-二烷基取代的芳基异腈与 N-propargyl-6-iodopyridones 的反应提供了具有显着区域选择性的 11H-indolizino[1,2-b]quinolin-9-ones，有利于更拥挤的产物。该方法的有用性通过 (20S)-7-三甲基甲硅烷基-9-异丙基喜树碱的区域选择性合成来说明。