(E)-2-(4-nitro-2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetic acid | 1267589-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(4-nitro-2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetic acid
• 英文别名: 2-[4-nitro-2-[(E)-3-oxo-3-phenylprop-1-enyl]phenoxy]acetic acid
• CAS: 1267589-07-0
• 化学式: C₁₇H₁₃NO₆
• 分子量: 327.293
• InChiKey: XPZQQAAFRPOWNH-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 (E)-2-(4-nitro-2-(3-oxo-3-phenylprop-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73%的产率得到(2R,3S)-methyl-5-nitro-3-(2-oxo-2-phenylethyl)-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：

  2-溴苯乙酮 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.0h， 生成 (E)-2-(4-nitro-2-(3-oxo-3-phenylprop-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

文献信息

• Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations
  作者：Dorine Belmessieri、Louis C. Morrill、Carmen Simal、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/ja109975c

  日期：2011.3.2

  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).