methyl 6-ethenyl-1-hydroxy-7-(2-methoxy-2-oxoethyl)-5-oxo-2,3-dihydro-1H-indolizine-8-carboxylate | 178949-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 6-ethenyl-1-hydroxy-7-(2-methoxy-2-oxoethyl)-5-oxo-2,3-dihydro-1H-indolizine-8-carboxylate
• CAS: 178949-29-6
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: ZPTKPKMRTRUOHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-ethenyl-1-hydroxy-7-(2-methoxy-2-oxoethyl)-5-oxo-2,3-dihydro-1H-indolizine-8-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 methyl 6-hydroxy-4-methyl-3,10-dioxo-4,6,7,8-tetrahydro-1H-pyrano[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
• 作为产物：
  描述：

  methyl (2Z)-2-(3-hydroxypyrrolidin-2-ylidene)acetate 在 palladium diacetate 、 三(邻甲基苯基)磷 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 25.0~125.0 ℃ 、517.1 kPa 条件下， 反应 95.0h， 生成 methyl 6-ethenyl-1-hydroxy-7-(2-methoxy-2-oxoethyl)-5-oxo-2,3-dihydro-1H-indolizine-8-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.