(E)-2-(4-methyl-2-(3-oxobut-1-en-1-yl)phenoxy)acetic acid | 1267589-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-(4-methyl-2-(3-oxobut-1-en-1-yl)phenoxy)acetic acid
• CAS: 1267589-13-8
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: BQHRAXIBBSUULK-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 (E)-2-(4-methyl-2-(3-oxobut-1-en-1-yl)phenoxy)acetic acid 在 三甲基乙酰氯 、 盐酸左旋咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以62%的产率得到(2R,3S)-methyl 5-methyl-3-(2-oxopropyl)-2,3-dihydrobenzofuran-2-carboxylate
  参考文献：
  名称：

  Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations

  摘要：

  Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

  DOI：

  10.1021/ja109975c
• 作为产物：
  描述：

  5-甲基水杨醛 在 水 、 caesium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E)-2-(4-methyl-2-(3-oxobut-1-en-1-yl)phenoxy)acetic acid
  参考文献：
  名称：

  Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations

  摘要：

  Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

  DOI：

  10.1021/ja109975c