3-(4-甲酰基苯基)-3-羟基丙酸乙酯 | 1000705-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-甲酰基苯基)-3-羟基丙酸乙酯
• 英文名称: ethyl 3-(4-formylphenyl)-3-hydroxypropanoate
• CAS: 1000705-84-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: ZICLYPLSPMPOMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-甲酰基苯基)-3-羟基丙酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 以322.2 mg的产率得到6,6'-benzene-1,4-diylbis(4-hydroxy-5,6-dihydro-2H-pyran-2-one)
  参考文献：
  名称：

  A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction

  摘要：

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.079
• 作为产物：
  描述：

  对苯二甲醛 、 bromozinc(1+),ethyl acetate 在 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-甲酰基苯基)-3-羟基丙酸乙酯
  参考文献：
  名称：

  A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction

  摘要：

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.079

文献信息

• Solvent-Free Synthesis of β-Hydroxy Esters and β-Amino Esters by Indium-Mediated Reformatsky Reaction
  作者：Huayue Wu、Weike Su、Xi’an Chen、Changfu Zhang、Xiaochun Yu、Jiang Cheng

  DOI：10.1055/s-2007-990799

  日期：2007.10

  In a convenient and efficient procedure for the solvent-free synthesis of β-hydroxy esters and β-amino esters, various aldehydes and aldimines undergo a Reformatsky reaction mediated by non-activated indium at room temperature to give the corresponding esters in good to excellent yields.

  在无溶剂合成 β-羟基酯和 β-氨基酯的方便有效的过程中，各种醛和醛亚胺在室温下发生由非活化铟介导的 Reformatsky 反应，以良好至极好的收率得到相应的酯.
• A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through double Reformatsky reaction
  作者：Masahiro Mineno、Yasuhiro Sawai、Kazuaki Kanno、Naotaka Sawada、Hideya Mizufune

  DOI：10.1016/j.tet.2013.10.079

  日期：2013.12

  A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to delta-hydroxy-beta-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and beta-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin. (C) 2013 Elsevier Ltd. All rights reserved.