Methyl 4-(1-hydroxy-4-phenylbut-3-yn-2-yl)benzoate | 823175-11-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Methyl 4-(1-hydroxy-4-phenylbut-3-yn-2-yl)benzoate
• 英文别名: methyl 4-(1-hydroxy-4-phenylbut-3-yn-2-yl)benzoate
• CAS: 823175-11-7
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: PNBKSZGOWXHSPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙炔 、 methyl 4-(oxiran-2-yl)benzoate 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 Methyl 4-(1-hydroxy-4-phenylbut-3-yn-2-yl)benzoate 、 methyl 4-(1-hydroxy-4-phenylbut-3-yn-1-yl)benzoate
  参考文献：
  名称：

  Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

  摘要：

  The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF3 mediated lithium acetylide provided either the alpha- or beta-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the beta- and alpha-products, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.049

文献信息

• Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides
  作者：Mitsuru Shindo、Tomoyuki Sugioka、Kozo Shishido

  DOI：10.1016/j.tetlet.2004.10.049

  日期：2004.12

  The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF3 mediated lithium acetylide provided either the alpha- or beta-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the beta- and alpha-products, respectively. (C) 2004 Elsevier Ltd. All rights reserved.