2-甲基-3-苯氧基丙酸乙酯 | 646064-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-甲基-3-苯氧基丙酸乙酯
• 英文名称: ethyl 2-methyl-3-phenoxypropanoate
• 英文别名: Propanoic acid, 2-methyl-3-phenoxy-, ethyl ester
• CAS: 646064-56-4
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CPDSKZDSSZKMMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  297.7±23.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-3-苯氧基丙酸乙酯 在 三氟甲磺酸 作用下， 反应 4.5h， 以95%的产率得到3-甲基-2,3-二氢-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095
• 作为产物：
  描述：

  ethyl 2-(phenoxymethyl)acrylate 在 palladium on activated charcoal 氢气 作用下， 以 乙腈 为溶剂， 以92%的产率得到2-甲基-3-苯氧基丙酸乙酯
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095

文献信息

• Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb Under Syngas Conditions
  作者：Manuel Amézquita-Valencia、Howard Alper

  DOI：10.1021/acs.joc.6b00522

  日期：2016.5.6

  A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

  报道了苯氧基酯和苯硫基酯的简单且区域选择性的合成。该产品由通过Pd催化的选择性烷氧基羰基而获得2（DBA）3，1,4-双（diphenylphisphino）丁烷（DPPB）的合成气（CO / H，和2）的氯仿/醇。这种方法可提供双收率好的产品，并具有出色的n选择性，并且无需使用添加剂。
• Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step
  作者：Olivier Roy、François Loiseau、Abdelkhalek Riahi、Françoise Hénin、Jacques Muzart

  DOI：10.1016/j.tet.2003.09.095

  日期：2003.11

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.