7-(2-Formyl-3,5-dihydroxy-4-methyl-phenyl)-hept-6-ynoic acid ethyl ester | 859507-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-Formyl-3,5-dihydroxy-4-methyl-phenyl)-hept-6-ynoic acid ethyl ester
• 英文别名: Ethyl 7-(2-formyl-3,5-dihydroxy-4-methylphenyl)hept-6-ynoate；ethyl 7-(2-formyl-3,5-dihydroxy-4-methylphenyl)hept-6-ynoate
• CAS: 859507-85-0
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: PKDQPWKMZQQCQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(2-Formyl-3,5-dihydroxy-4-methyl-phenyl)-hept-6-ynoic acid ethyl ester 在 4-二甲氨基吡啶 Cu₂[(-)-sparteine]2O₂ 、 氧气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 7-{(R)-4-Hydroxy-6-[1-hydroxy-meth-(Z)-ylidene]-4-methyl-3,5-dioxo-cyclohex-1-enyl}-hept-6-ynoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization

  摘要：

  An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.

  DOI：

  10.1021/ja052049g
• 作为产物：
  描述：

  2-庚酸乙酯 、 6-bromo-2,4-dihydroxy-3-methylbenzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以81%的产率得到7-(2-Formyl-3,5-dihydroxy-4-methyl-phenyl)-hept-6-ynoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization

  摘要：

  An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.

  DOI：

  10.1021/ja052049g

文献信息

• Synthesis of the Azaphilones Using Copper-Mediated Enantioselective Oxidative Dearomatization
  作者：Jianglong Zhu、Nicholas P. Grigoriadis、Jonathan P. Lee、John A. Porco

  DOI：10.1021/ja052049g

  日期：2005.7.1

  An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.