5-(tert-butyldimethylsilyl)-3-isobutoxy-2-methylpent-2-en-4-ynoic acid | 1197324-64-3

• 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: 5-(tert-butyldimethylsilyl)-3-isobutoxy-2-methylpent-2-en-4-ynoic acid
• 英文别名: (E)-5-[tert-butyl(dimethyl)silyl]-2-methyl-3-(2-methylpropoxy)pent-2-en-4-ynoic acid
• CAS: 1197324-64-3
• 化学式: C₁₆H₂₈O₃Si
• 分子量: 296.482
• InChiKey: LNZUPCPUQXUYPH-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilyl)-3-isobutoxy-2-methylpent-2-en-4-ynoic acid 在 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以93%的产率得到(Z)-5-((tert-butyldimethylsilyl)methylene)-4-isobutoxy-3-methylfuran-2(5H)-one
  参考文献：
  名称：

  Stereoselective Synthesis of (E)-2-En-4-ynoic Acids with Ynolates: Catalytic Conversion to Tetronic Acids and 2-Pyrones

  摘要：

  A highly torquoselective olefination of alkynoates to provide functionalized tetrasubstituted olefins, (E)-2-en-4-ynoic acids, is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.

  DOI：

  10.1021/ol902086t
• 作为产物：
  描述：

  ethyl 2,2-dibromopropanoate 、 isobutyl 3-(tert-butyldimethylsilyl)propiolate 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以63%的产率得到5-(tert-butyldimethylsilyl)-3-isobutoxy-2-methylpent-2-en-4-ynoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of (E)-2-En-4-ynoic Acids with Ynolates: Catalytic Conversion to Tetronic Acids and 2-Pyrones

  摘要：

  A highly torquoselective olefination of alkynoates to provide functionalized tetrasubstituted olefins, (E)-2-en-4-ynoic acids, is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.

  DOI：

  10.1021/ol902086t

文献信息

• Stereoselective Synthesis of (<i>E</i>)-2-En-4-ynoic Acids with Ynolates: Catalytic Conversion to Tetronic Acids and 2-Pyrones
  作者：Takashi Yoshikawa、Mitsuru Shindo

  DOI：10.1021/ol902086t

  日期：2009.12.3

  A highly torquoselective olefination of alkynoates to provide functionalized tetrasubstituted olefins, (E)-2-en-4-ynoic acids, is described. Addition of Bronsted acids dramatically switched the mode of the Ag(l)-catalyzed cyclization of the resulting enyne carboxylic acids to give either tetronic acids or 2-pyrones.