ethyl 2-(2-formyl-6-methylphenoxy)acetate | 303225-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(2-formyl-6-methylphenoxy)acetate
• CAS: 303225-16-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: FFZYTUKHCRPLMR-UHFFFAOYSA-N

物化性质

• 熔点：
  38-40 °C
• 沸点：
  333.1±27.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-formyl-6-methylphenoxy)acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 生成 (E)-2-(2-methyl-6-(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
• 作为产物：
  描述：

  2-羟基-3-甲基苯甲醛 、 溴乙酸乙酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以93%的产率得到ethyl 2-(2-formyl-6-methylphenoxy)acetate
  参考文献：
  名称：

  Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

  摘要：

  Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr(2)NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.

  DOI：

  10.1021/acs.orglett.5b02997

文献信息

• Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization
  作者：Alison J. Fugard、Bethany K. Thompson、Alexandra M. Z. Slawin、James E. Taylor、Andrew D. Smith

  DOI：10.1021/acs.orglett.5b02997

  日期：2015.12.4

  Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr(2)NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.
• 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).