[3-(Benzotriazol-1-yl)-3-ethoxy-2-phenylpent-4-en-2-yl]oxy-trimethylsilane | 1026561-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: [3-(Benzotriazol-1-yl)-3-ethoxy-2-phenylpent-4-en-2-yl]oxy-trimethylsilane
• CAS: 1026561-05-6
• 化学式: C₂₂H₂₉N₃O₂Si
• 分子量: 395.577
• InChiKey: FOWPINAQQVXPDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 [3-(Benzotriazol-1-yl)-3-ethoxy-2-phenylpent-4-en-2-yl]oxy-trimethylsilane 在 盐酸 作用下， 生成 2-hydroxy-2-phenylhexan-3-one
  参考文献：
  名称：

  Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines

  摘要：

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.

  DOI：

  10.1021/jo00128a037
• 作为产物：
  描述：

  1-(1-乙氧基-2-丙烯-1-基)-1H-苯并三唑 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 16.08h， 生成 [3-(Benzotriazol-1-yl)-3-ethoxy-2-phenylpent-4-en-2-yl]oxy-trimethylsilane
  参考文献：
  名称：

  Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines

  摘要：

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.

  DOI：

  10.1021/jo00128a037

文献信息

• Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines
  作者：Alan R. Katritzky、Guifen Zhang、Jinlong Jiang

  DOI：10.1021/jo00128a037

  日期：1995.11

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.