methyl (2E)-3-[5-((Z)-2-hydroxyethylidene)-2-oxo-5,6-dihydro-2H-pyran-3-yl]acrylate | 1094561-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (2E)-3-[5-((Z)-2-hydroxyethylidene)-2-oxo-5,6-dihydro-2H-pyran-3-yl]acrylate
• 英文别名: methyl (E)-3-[(5Z)-5-(2-hydroxyethylidene)-2-oxopyran-3-yl]prop-2-enoate
• CAS: 1094561-84-8
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: SXYSDOHKDKMTTA-HOJFPOIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-3-碘丙烯酸甲酯 、 methyl (Z)-6-(tetrahydro-2H-pyran-2-yloxy)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]hex-4-en-2-ynoate 在 四(三苯基膦)钯 、 三正丁基氢锡 、 Dowex 50 、 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.08h， 生成 methyl (2E)-3-[5-((Z)-2-hydroxyethylidene)-2-oxo-5,6-dihydro-2H-pyran-3-yl]acrylate
  参考文献：
  名称：

  A Short Entry to α-Substituted γ-Alkylidene Pentenolides. Synthesis and Preliminary Biological Evaluation of Novel Gelastatin Analogues

  摘要：

  Biologically interesting 2-substituted 4-alkylidene pentenolides were prepared with complete control of regio- and stereoselectivity from 2-iodo allylic alcohols via an array of Pd-catalyzed processes, including alkynylation with methyl propiolate, tributyltin hydride addition, and alpha-functionalization. Some of the compounds possess selective cytostatic activity against ovarian carcinoma HeLa S3 and leukemia CCRF-CEM cell lines.

  DOI：

  10.1021/jo802082t

文献信息

• A Short Entry to α-Substituted γ-Alkylidene Pentenolides. Synthesis and Preliminary Biological Evaluation of Novel Gelastatin Analogues
  作者：Jan Pavlík、Ivan Šnajdr、Jiří Kuneš、Marcel Špulák、Milan Pour

  DOI：10.1021/jo802082t

  日期：2009.1.16

  Biologically interesting 2-substituted 4-alkylidene pentenolides were prepared with complete control of regio- and stereoselectivity from 2-iodo allylic alcohols via an array of Pd-catalyzed processes, including alkynylation with methyl propiolate, tributyltin hydride addition, and alpha-functionalization. Some of the compounds possess selective cytostatic activity against ovarian carcinoma HeLa S3 and leukemia CCRF-CEM cell lines.