(Z)-1-trimethylsilyloct-3-en-1-yn-5-ol | 250358-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-trimethylsilyloct-3-en-1-yn-5-ol
• 英文别名: (Z)-8-trimethylsilyloct-5-en-7-yn-4-ol
• CAS: 250358-24-8
• 化学式: C₁₁H₂₀OSi
• 分子量: 196.365
• InChiKey: IEWRSXGHRZKGCN-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-trimethylsilyloct-3-en-1-yn-5-ol 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (Z)-oct-3-en-1-yn-5-ol
  参考文献：
  名称：

  An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (Z)-2-En-4-yn-1-ols

  摘要：

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.

  DOI：

  10.1021/jo990848+
• 作为产物：
  描述：

  (Z)-1-iodohex-1-en-3-ol 、 三甲基乙炔基硅 在 四(三苯基膦)钯 四氢吡咯 、 copper(l) iodide 作用下， 反应 5.0h， 以95%的产率得到(Z)-1-trimethylsilyloct-3-en-1-yn-5-ol
  参考文献：
  名称：

  An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (Z)-2-En-4-yn-1-ols

  摘要：

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.

  DOI：

  10.1021/jo990848+

文献信息

• An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1021/jo990848+

  日期：1999.10.1

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.