Methyl 4-methyl-3,6,10-trioxo-1,4,7,8-tetrahydropyrano[3,4-f]indolizine-5-carboxylate | 178949-32-1

• 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: Methyl 4-methyl-3,6,10-trioxo-1,4,7,8-tetrahydropyrano[3,4-f]indolizine-5-carboxylate
• CAS: 178949-32-1
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: KXUOBXMOXVBXAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4-methyl-3,6,10-trioxo-1,4,7,8-tetrahydropyrano[3,4-f]indolizine-5-carboxylate 在 吡啶 、 甲醇 、 氢溴酸 、 双氧水 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 57.0h， 生成 18-Noranhydrocamptothecin
  参考文献：
  名称：

  Synthesis of 18-Noranhydrocamptothecin Analogs Which Retain Topoisomerase I Inhibitory Function

  摘要：

  The total syntheses of compounds 2 and 3 are described. Key departures from previous routes to camptothecin from these laboratories involved (i) early incorporation of C-2 oxygen (see compound 9) and (ii) recourse to a Heck vinylation for installation of a hydroxymethyl equivalent on the pyridone (see transformation 15 --> 16). The final compounds are of considerable interest in that they are the most drastically modified E ring systems which retain topoisomerase I inhibitory function.

  DOI：

  10.1021/jo00102a030
• 作为产物：
  描述：

  methyl 6-hydroxy-4-methyl-3,10-dioxo-4,6,7,8-tetrahydro-1H-pyrano[3,4-f]indolizine-5-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到Methyl 4-methyl-3,6,10-trioxo-1,4,7,8-tetrahydropyrano[3,4-f]indolizine-5-carboxylate
  参考文献：
  名称：

  Synthesis of 18-Noranhydrocamptothecin Analogs Which Retain Topoisomerase I Inhibitory Function

  摘要：

  The total syntheses of compounds 2 and 3 are described. Key departures from previous routes to camptothecin from these laboratories involved (i) early incorporation of C-2 oxygen (see compound 9) and (ii) recourse to a Heck vinylation for installation of a hydroxymethyl equivalent on the pyridone (see transformation 15 --> 16). The final compounds are of considerable interest in that they are the most drastically modified E ring systems which retain topoisomerase I inhibitory function.

  DOI：

  10.1021/jo00102a030

文献信息

• Synthesis of 18-Noranhydrocamptothecin Analogs Which Retain Topoisomerase I Inhibitory Function
  作者：Lawrence Snyder、Wang Shen、William G. Bornmann、Samuel J. Danishefsky

  DOI：10.1021/jo00102a030

  日期：1994.11

  The total syntheses of compounds 2 and 3 are described. Key departures from previous routes to camptothecin from these laboratories involved (i) early incorporation of C-2 oxygen (see compound 9) and (ii) recourse to a Heck vinylation for installation of a hydroxymethyl equivalent on the pyridone (see transformation 15 --> 16). The final compounds are of considerable interest in that they are the most drastically modified E ring systems which retain topoisomerase I inhibitory function.