6-benzyloxyhex-2-ynoic acid methyl ester | 824948-18-7

• 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: 6-benzyloxyhex-2-ynoic acid methyl ester
• 英文别名: Methyl 6-(benzyloxy)hex-3-ynoate；methyl 6-phenylmethoxyhex-3-ynoate
• CAS: 824948-18-7
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: CLAUCANUVLWTAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  6-benzyloxy-hex-2-ynoic acid methyl ester 在 六甲基磷酰三胺 、 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以51%的产率得到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.