(E)-2-hydroxy-2-phenyloct-3-enoic acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-hydroxy-2-phenyloct-3-enoic acid methyl ester
• 英文别名: methyl (E)-2-hydroxy-2-phenyloct-3-enoate
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: ODMDWKOTFDEGEQ-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  苯甲酰甲酸甲酯 、 1-己炔 在 Schwartz's reagent 、 Dimethylzinc 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 以93%的产率得到(E)-2-hydroxy-2-phenyloct-3-enoic acid methyl ester
  参考文献：
  名称：

  Dimethylzinc-Mediated Addition of Alkenylzirconocenes to α-Keto and α-Imino Esters

  摘要：

  graphicHydrozirconation of alkynes followed by in situ transmetalation to dimethylzinc and 1,2-addition to activated ketones and N-diphenylphosphinoylimines leads to tertiary allylic alcohols and amines in high overall yield. With 8-phenylmenthol as the chiral auxiliary, si-face attack proceeds in good to excellent diastereoselectivitles.

  DOI：

  10.1021/ol0347141

文献信息

• Dimethylzinc-Mediated Addition of Alkenylzirconocenes to α-Keto and α-Imino Esters
  作者：Peter Wipf、Corey R. J. Stephenson

  DOI：10.1021/ol0347141

  日期：2003.7.1

  graphicHydrozirconation of alkynes followed by in situ transmetalation to dimethylzinc and 1,2-addition to activated ketones and N-diphenylphosphinoylimines leads to tertiary allylic alcohols and amines in high overall yield. With 8-phenylmenthol as the chiral auxiliary, si-face attack proceeds in good to excellent diastereoselectivitles.