(R)-2-(naphthalen-2-yl)-5-(trimethylsilyl)pent-4-yn-2-ol | 1312791-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(naphthalen-2-yl)-5-(trimethylsilyl)pent-4-yn-2-ol
• CAS: 1312791-21-1
• 化学式: C₁₈H₂₂OSi
• 分子量: 282.458
• InChiKey: UXWVHLVPDIFUBQ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-2-(naphthalen-2-yl)-5-(trimethylsilyl)pent-4-yn-2-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到(R)-(+)-2-(naphthalen-2-yl)pent-4-yn-2-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
• 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 、 2-萘乙酮 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 15.0h， 以96%的产率得到(R)-2-(naphthalen-2-yl)-5-(trimethylsilyl)pent-4-yn-2-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