2-(2-Methoxy-phenoxymethyl)-acrylic acid ethyl ester | 646064-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-Methoxy-phenoxymethyl)-acrylic acid ethyl ester
• 英文别名: Ethyl 2-[(2-methoxyphenoxy)methyl]prop-2-enoate
• CAS: 646064-55-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ORJRFZCPRXPYMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Methoxy-phenoxymethyl)-acrylic acid ethyl ester 在 palladium on activated charcoal 甲烷磺酸 、 氢气 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 8-methoxy-3-methylchroman-4-one
  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

• 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.