2-[hydroxy-(3-hydroxyphenyl)methyl]buta-2,3-dienoic acid ethyl ester | 1041333-56-5

• 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: 2-[hydroxy-(3-hydroxyphenyl)methyl]buta-2,3-dienoic acid ethyl ester
• CAS: 1041333-56-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DATFZNHZIGGYDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[hydroxy-(3-hydroxyphenyl)methyl]buta-2,3-dienoic acid ethyl ester 在 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到2-(3-hydroxyphenyl)-3-ethoxycarbonyl-2,5-dihydrofuran
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-Endo Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans

  摘要：

  Ethyl alpha-(1-hydroxy-1-alkyl)methylallenoates and alpha-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the alpha-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbony1-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.

  DOI：

  10.1021/jo2018125
• 作为产物：
  描述：

  ethyl 4-bromobut-2-ynoate 、 间羟基苯甲醛 在 indium 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 以65%的产率得到2-[hydroxy-(3-hydroxyphenyl)methyl]buta-2,3-dienoic acid ethyl ester
  参考文献：
  名称：

  Indium-Mediated Regio- and Chemoselective Synthesis of α-Hydroxyalkyl Allenic Esters and Gold-Catalyzed Cyclizations to Ethyl 2-Naphthoate Derivatives

  摘要：

  The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.

  DOI：

  10.1021/ol801196g