Trimethyl-(5-methyl-1-phenylhex-4-en-1-yn-3-yl)oxysilane | 1133296-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Trimethyl-(5-methyl-1-phenylhex-4-en-1-yn-3-yl)oxysilane
• 英文别名: trimethyl-(5-methyl-1-phenylhex-4-en-1-yn-3-yl)oxysilane
• CAS: 1133296-10-2
• 化学式: C₁₆H₂₂OSi
• 分子量: 258.436
• InChiKey: HBWSFTDATXHEBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 Trimethyl-(5-methyl-1-phenylhex-4-en-1-yn-3-yl)oxysilane 在 potassium tetrachloroaurate(III) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 以68%的产率得到(E)-1-(5-methoxy-5-methylhex-3-en-1-ynyl)benzene
  参考文献：
  名称：

  Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

  摘要：

  Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Bronsted- and Lewis-acids, although scope and yields are markedly reduced. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.062
• 作为产物：
  描述：

  5-Methyl-1-phenylhex-4-en-1-yn-3-ol 生成 Trimethyl-(5-methyl-1-phenylhex-4-en-1-yn-3-yl)oxysilane
  参考文献：
  名称：

  Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

  摘要：

  Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Bronsted- and Lewis-acids, although scope and yields are markedly reduced. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.062

文献信息

• Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution
  作者：Timm T. Haug、Tobias Harschneck、Alexander Duschek、Chang-Uk Lee、Jörg T. Binder、Helge Menz、Stefan F. Kirsch

  DOI：10.1016/j.jorganchem.2008.09.062

  日期：2009.2

  Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Bronsted- and Lewis-acids, although scope and yields are markedly reduced. (C) 2008 Elsevier B.V. All rights reserved.