(E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoic acid | 853055-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoic acid
• CAS: 853055-27-3
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: KCNUYJVSICNUKE-VOTSOKGWSA-N

物化性质

• 沸点：
  389.7±32.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoyl chloride
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584
• 作为产物：
  描述：

  (E)-methyl 3-(4-methoxybenzyloxy)acrylate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以62%的产率得到(E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoic acid
  参考文献：
  名称：

  The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone

  摘要：

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.027

文献信息

• The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone
  作者：Nessan J. Kerrigan、Tejas Upadhyay、David J. Procter

  DOI：10.1016/j.tetlet.2004.10.027

  日期：2004.11

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.
• Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid
  作者：Mukund P. Sibi、Takahiro Soeta、Craig P. Jasperse

  DOI：10.1021/ol9018584

  日期：2009.12.3

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.