5-(trimethoxyphenyl)-4-(trimethylsilyl)pent-1-yn-3-ol | 429680-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(trimethoxyphenyl)-4-(trimethylsilyl)pent-1-yn-3-ol
• 英文别名: 5-(3-Methoxyphenyl)-1-trimethylsilylpent-1-yn-3-ol
• CAS: 429680-31-9
• 化学式: C₁₅H₂₂O₂Si
• 分子量: 262.424
• InChiKey: MMDMSZWPVNSWCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(trimethoxyphenyl)-4-(trimethylsilyl)pent-1-yn-3-ol 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 盐酸 、 四氯化锡 、 sodium naphthalenide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.66h， 生成 (7E)-3-methoxy-8-(trimethylsilylmethyl)-6,9,10,11-tetrahydro-5H-benzo[9]annulen-11-ol
  参考文献：
  名称：

  Atom-Efficient Assembly of 1,5-Oxygen-Bridged Medium-Sized Carbocycles by Sequential Combination of a Ru-Catalyzed Alkyne−Alkene Coupling and a Prins-Type Cyclization

  摘要：

  Ruthenium-catalyzed coupling of readily accessible 1-trimethylsilyl-1-alkyn-3-ols to allyl ethyl ether followed by in situ ketalization and Lewis-acid induced cyclization affords 1,5-oxygen-bridged eight- and nine-membered carbocycles, products which are difficult to construct with previously published strategies.

  DOI：

  10.1021/ja017804e
• 作为产物：
  描述：

  3-(3-甲氧基苯基)丙醛 、 三甲基乙炔基硅 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以95%的产率得到5-(trimethoxyphenyl)-4-(trimethylsilyl)pent-1-yn-3-ol
  参考文献：
  名称：

  Atom-Efficient Assembly of 1,5-Oxygen-Bridged Medium-Sized Carbocycles by Sequential Combination of a Ru-Catalyzed Alkyne−Alkene Coupling and a Prins-Type Cyclization

  摘要：

  Ruthenium-catalyzed coupling of readily accessible 1-trimethylsilyl-1-alkyn-3-ols to allyl ethyl ether followed by in situ ketalization and Lewis-acid induced cyclization affords 1,5-oxygen-bridged eight- and nine-membered carbocycles, products which are difficult to construct with previously published strategies.

  DOI：

  10.1021/ja017804e

文献信息

• Practical Asymmetric Approach to Medium-Sized Carbocycles Based on the Combination of Two Ru-Catalyzed Transformations and a Lewis Acid-Induced Cyclization
  作者：Fernando López、Luis Castedo、José L. Mascareñas

  DOI：10.1021/ol0477125

  日期：2005.1.1

  [Reaction: see text] Ruthenium-catalyzed coupling of allyl ethyl ether to optically active 1-trimethylsilyl-1-alkyn-3-ols, followed by in situ ketalization and Lewis-acid-induced cyclization, affords enantiomerically pure 1,5-oxygen-bridged eight- and nine-membered carbocycles. Opening of the oxygen bridge under basic or electron transfer conditions provides optically pure medium-sized carbocycles

  [反应：参见文本]钌催化的烯丙基乙基醚与光学活性的1-trimethylsilyl-1-alkyn-3-ols偶联，然后进行原位缩酮化和Lewis酸诱导的环化反应，得到对映体纯的1,5-氧桥接的八元和九元摩托车。在碱性或电子转移条件下打开氧桥可提供光学纯的中型碳环化合物，这些产品很难使用其他当前可用的方法来构建。
• Atom-Efficient Assembly of 1,5-Oxygen-Bridged Medium-Sized Carbocycles by Sequential Combination of a Ru-Catalyzed Alkyne−Alkene Coupling and a <i>Prins</i>-Type Cyclization
  作者：Fernando López、Luis Castedo、José L. Mascareñas

  DOI：10.1021/ja017804e

  日期：2002.4.1

  Ruthenium-catalyzed coupling of readily accessible 1-trimethylsilyl-1-alkyn-3-ols to allyl ethyl ether followed by in situ ketalization and Lewis-acid induced cyclization affords 1,5-oxygen-bridged eight- and nine-membered carbocycles, products which are difficult to construct with previously published strategies.