1-(benzyloxy)-4-methylhept-2-yn-4-yl diethyl phosphate | 1324010-96-9

• 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: 1-(benzyloxy)-4-methylhept-2-yn-4-yl diethyl phosphate
• 英文别名: Diethyl (4-methyl-1-phenylmethoxyhept-2-yn-4-yl) phosphate；diethyl (4-methyl-1-phenylmethoxyhept-2-yn-4-yl) phosphate
• CAS: 1324010-96-9
• 化学式: C₁₉H₂₉O₅P
• 分子量: 368.41
• InChiKey: HMWHCCXBGPYNFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)-4-methylhept-2-yn-4-yl diethyl phosphate 、 (二甲基苯硅烷基)硼酸频那醇酯 在 sodium methylate 、 copper(l) cyanide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到1-benzyloxy-2-(dimethylphenylsilyl)-4-methyl-2,3-heptadiene
  参考文献：
  名称：

  Copper(I)-Catalyzed Regioselective Propargylic Substitution Involving Si–B Bond Activation

  摘要：

  The silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation allows several gamma-selective propargylic substitutions. The regioselectivity (gamma:alpha ratio) Is strongly dependent on the propargylic leaving group. Chloride Is superior to oxygen leaving groups in linear substrates (gamma:alpha > 99:1), and it is only the phosphate group that also shows promising regiocontrol (gamma:alpha = 90:10). That leaving group produces superb gamma-selectivity (gamma:alpha > 99:1) in alpha-branched propargylic systems, and enantioenriched substrates react with excellent central-to-axial chirality transfer.

  DOI：

  10.1021/ol201811d

文献信息

• Copper(I)-Catalyzed Regioselective Propargylic Substitution Involving Si–B Bond Activation
  作者：Devendra J. Vyas、Chinmoy K. Hazra、Martin Oestreich

  DOI：10.1021/ol201811d

  日期：2011.8.19

  The silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation allows several gamma-selective propargylic substitutions. The regioselectivity (gamma:alpha ratio) Is strongly dependent on the propargylic leaving group. Chloride Is superior to oxygen leaving groups in linear substrates (gamma:alpha > 99:1), and it is only the phosphate group that also shows promising regiocontrol (gamma:alpha = 90:10). That leaving group produces superb gamma-selectivity (gamma:alpha > 99:1) in alpha-branched propargylic systems, and enantioenriched substrates react with excellent central-to-axial chirality transfer.