(E)-phenyl 4-hydroxybut-2-enoate | 1376702-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (E)-phenyl 4-hydroxybut-2-enoate
• 英文别名: (E)-phenyl-4-hydroxybut-2-enoate；phenyl (E)-4-hydroxybut-2-enoate
• CAS: 1376702-19-0
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: IQYDCWAOTGGTPE-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-phenyl 4-hydroxybut-2-enoate 、 (E)-N-naphthalen-1-methylene-4-toluenesulfonamide 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.17h， 生成 phenyl 2-((2R,4R)-2-(naphthalene-1-yl)-3-tosyloxazolidin-4-yl)acetate
  参考文献：
  名称：

  Asymmetric Synthesis of 1,3-Oxazolidines via Intramolecular Aza-Michael Addition by Bifunctional Organocatalysts

  摘要：

  报告了一种通过在金鸡纳碱-硫脲基双功能有机催化剂存在下，进行形式[3 + 2]环加成合成光学活性1,3-氧杂环戊烷的新合成路线。该方法便于获得广泛的手性1,3-氧杂环戊烷。此外，结果表明，双功能有机催化剂能够实现分子内氮杂Michael加成，从而导致氮含杂环的非对称合成。

  DOI：

  10.1246/cl.121245
• 作为产物：
  描述：

  苯酚 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 19.08h， 生成 (E)-phenyl 4-hydroxybut-2-enoate
  参考文献：
  名称：

  Procedure-Controlled Enantioselectivity Switch in Organocatalytic 2-Oxazolidinone Synthesis

  摘要：

  In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.

  DOI：

  10.1021/ja407027e

文献信息

• Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates
  作者：Takaaki Okamura、Keisuke Asano、Seijiro Matsubara

  DOI：10.1039/c2cc31602a

  日期：——

  We report an asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.

  我们报道了一种通过金鸡纳生物碱硫脲基双功能有机催化剂存在下的半缩醛中间体，对γ-羟基-α,β-不饱和硫酯进行不对称氧迈克尔加成的反应。该方法为合成β-羟基羧酸化合物提供了一条新颖的手性选择性途径，而这些化合物又可用于合成有价值的手性构建基块。
• Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile
  作者：Naoki Yoneda、Ayano Hotta、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol503104b

  日期：2014.12.5

  Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to gamma-hydroxy-alpha,beta-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into beta-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of alpha,beta-unsaturated carbonyl compounds.