(E)-3-(4-methoxy-2-(3-oxobut-1-en-1-yl)phenyl)propanoic acid | 1267588-95-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (E)-3-(4-methoxy-2-(3-oxobut-1-en-1-yl)phenyl)propanoic acid
• CAS: 1267588-95-3
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: YGDKYDGQVSRIGW-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (E)-3-(4-methoxy-2-(3-oxobut-1-en-1-yl)phenyl)propanoic 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 16.3h， 以43%的产率得到(4aR,9aR)-6-methoxy-3-methyl-9,9a-dihydroindeno[2,1-c]pyran-1(4aH)-one
  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：

  7-甲氧基-2-萘满酮 在 氧气 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.25h， 生成 (E)-3-(4-methoxy-2-(3-oxobut-1-en-1-yl)phenyl)propanoic 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