2,2-dibenzyl-6-benzyloxyhex-2-ynoic acid methyl ester

• 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: 2,2-dibenzyl-6-benzyloxyhex-2-ynoic acid methyl ester
• 英文别名: Methyl 2,2-dibenzyl-6-phenylmethoxyhex-3-ynoate
• 化学式: C₂₈H₂₈O₃
• 分子量: 412.529
• InChiKey: AXMNBDKWZSCIKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 、 6-benzyloxy-hex-2-ynoic acid methyl ester 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到2,2-dibenzyl-6-benzyloxyhex-2-ynoic acid methyl ester
  参考文献：
  名称：

  Deconjugative Conversion of α-Alkynyl Esters to α,α-Disubstituted β-Alkynyl Esters

  摘要：

  We report the development of a method for the conversion of a variety of conjugated alpha-alkynyl esters to alpha,alpha-disubstituted beta-alkynylesters through the use of strong amide bases. Studies indicate that the second equivalent of base leads to the dianion intermediate. Optimal conditions included the use of 2 equiv of lithium diisopropylamide in THF with HMPA as the cosolvent followed by trapping with a variety of carbon electrophiles. Trapping with bis-electrophiles leads to spiro cycloalkane products.

  DOI：

  10.1021/jo050218+

文献信息

• Deconjugative Conversion of α-Alkynyl Esters to α,α-Disubstituted β-Alkynyl Esters
  作者：Salvatore D. Lepore、Yuanjun He

  DOI：10.1021/jo050218+

  日期：2005.5.1

  We report the development of a method for the conversion of a variety of conjugated alpha-alkynyl esters to alpha,alpha-disubstituted beta-alkynylesters through the use of strong amide bases. Studies indicate that the second equivalent of base leads to the dianion intermediate. Optimal conditions included the use of 2 equiv of lithium diisopropylamide in THF with HMPA as the cosolvent followed by trapping with a variety of carbon electrophiles. Trapping with bis-electrophiles leads to spiro cycloalkane products.