methyl (Z)-6-(tetrahydro-2H-pyran-2-yloxy)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]hex-4-en-2-ynoate | 1094561-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-6-(tetrahydro-2H-pyran-2-yloxy)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]hex-4-en-2-ynoate
• 英文别名: methyl (Z)-6-(oxan-2-yloxy)-4-(oxan-2-yloxymethyl)hex-4-en-2-ynoate
• CAS: 1094561-68-8
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: QULWWANODWJXKH-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (Z)-6-(tetrahydro-2H-pyran-2-yloxy)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]hex-4-en-2-ynoate 、 (E)-1-tert-butyldimethylsilyloxy-3-iodo-2-propene 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 (5Z)-3-[(E)-3-(tert-butyldimethylsilyloxy)prop-1-enyl]-5-(2-hydroxyethylidene)-5,6-dihydro-2H-pyran-2-one
  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
• 作为产物：
  描述：

  2-[(E)-2-iodo-4-(oxan-2-yloxy)but-2-enoxy]oxane 、 丙炔酸甲酯 在 正丁基锂 、 (tris(2-furyl)phosphine)2PdCl2 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72%的产率得到methyl (Z)-6-(tetrahydro-2H-pyran-2-yloxy)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]hex-4-en-2-ynoate
  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.