(S)-3-methyl-6-(trimethylsilyl)hex-5-yn-3-ol | 1312791-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-methyl-6-(trimethylsilyl)hex-5-yn-3-ol
• 英文别名: (3S)-3-methyl-6-trimethylsilylhex-5-yn-3-ol
• CAS: 1312791-09-5
• 化学式: C₁₀H₂₀OSi
• 分子量: 184.354
• InChiKey: USHOOUQQMRZENP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (S)-3-methyl-6-(trimethylsilyl)hex-5-yn-3-ol 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 醋酸异丙酯 、 水 为溶剂， 反应 29.0h， 生成 (S)-3-(benzoyloxy)-3-methylpentanoic acid
  参考文献：
  名称：

  A General Copper–BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates

  摘要：

  An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.

  DOI：

  10.1021/ja2028958
• 作为产物：
  描述：

  trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 、 丁酮 在 copper(II) isobutyrate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以83%的产率得到(S)-3-methyl-6-(trimethylsilyl)hex-5-yn-3-ol
  参考文献：
  名称：

  A General Copper–BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates

  摘要：

  An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.

  DOI：

  10.1021/ja2028958

文献信息

• A General Copper–BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates
  作者：Keith R. Fandrick、Daniel R. Fandrick、Jonathan T. Reeves、Joe Gao、Shengli Ma、Wenjie Li、Heewon Lee、Nelu Grinberg、Bruce Lu、Chris H. Senanayake

  DOI：10.1021/ja2028958

  日期：2011.7.13

  An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.