2,3-dideuterio-3-(4-hydroxyphenyl)propionic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2,3-dideuterio-3-(4-hydroxyphenyl)propionic acid
• 英文别名: 2,3-Dideuterio-3-(4-hydroxyphenyl)propanoic acid；2,3-dideuterio-3-(4-hydroxyphenyl)propanoic acid
• 化学式: C₉H₁₀O₃
• 分子量: 168.161
• InChiKey: NMHMNPHRMNGLLB-OMYOYQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-香豆酸 在 samarium diiodide 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以71%的产率得到2,3-dideuterio-3-(4-hydroxyphenyl)propionic acid
  参考文献：
  名称：

  Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O

  摘要：

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.

  DOI：

  10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u

文献信息

• Synthesis of Different Deuterated Carboxylic Acids from Unsaturated Acids Promoted by Samarium Diiodide and D2O
  作者：José M. Concellón、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20021004)8:19<4493::aid-chem4493>3.0.co;2-u

  日期：2002.10.4

  An easy, and rapid reduction of the C=C bond of alpha,beta-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-alpha,delta-dideuterio-betagamma-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-beta,gamma-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.