methyl (2Z)-2-(3-hydroxypyrrolidin-2-ylidene)acetate | 159021-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (2Z)-2-(3-hydroxypyrrolidin-2-ylidene)acetate
• CAS: 159021-79-1
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: MJAPDZNNWGSRCA-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-2-(3-hydroxypyrrolidin-2-ylidene)acetate 在 硫酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 115.5h， 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：

  甲醇 、 [2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)pyrrolidin-3-yl] acetate 在 sodium methylate 作用下， 反应 17.0h， 以81%的产率得到methyl (2Z)-2-(3-hydroxypyrrolidin-2-ylidene)acetate
  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.