ethyl (Z)-2-(4-methoxybenzylidene)-3-methylbutanoate | 1256556-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (Z)-2-(4-methoxybenzylidene)-3-methylbutanoate
• CAS: 1256556-49-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: IYVSMSIPHCWTRH-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  异丙基丙二酸二乙酯 在 吗啉 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 ethyl (E)-2-(4-methoxybenzylidene)-3-methylbutanoate 、 ethyl (Z)-2-(4-methoxybenzylidene)-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of α,β-Disubstituted Acrylates via Galat Reaction

  摘要：

  Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse alpha,beta-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.

  DOI：

  10.1021/acs.orglett.9b02291

文献信息

• Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
  作者：Goffredo Rosini、Claudio Paolucci、Francesca Boschi、Emanuela Marotta、Paolo Righi、Francesco Tozzi

  DOI：10.1039/c0gc00013b

  日期：——

  Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α-aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.

  对映体的α-可互变和未功能化的醛通过以下步骤转化为富含对映体的混合物：(i) 与(R)-或(S)-1-(α-氨基苄基)-2-萘酚（Betti碱）反应，转化为二面体异构体的3-取代1-苯基-2,3-二氢-1H-萘并[1,2-e][1,3]氧杂啉；(ii) 促酸的结晶诱导二面体异构体转化（CIDT）；(iii) 清洁地切割富集的二面体异构体的二氢-1,3-萘氧杂烯环，易于过滤收集，从而回收富含对映体的醛和手性辅助剂。