2-phenyl-3,3-d2-propanoic acid | 1386447-04-6

• 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-phenyl-3,3-d2-propanoic acid
• 英文别名: 3,3-Dideuterio-2-phenylpropanoic acid；3,3-dideuterio-2-phenylpropanoic acid
• CAS: 1386447-04-6
• 化学式: C₉H₁₀O₂
• 分子量: 152.161
• InChiKey: YPGCWEMNNLXISK-DICFDUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙烯 在 2,6-双[1-(2,6-二异丙苯亚氨基)乙基]吡啶 、 氘代溴乙烷 、 magnesium 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 2-苯基丙酸 、 2-phenyl-3,3-d2-propanoic acid 、 (+/-)-3,3,3-trideuterio-2-phenylpropanoic acid 、 3-[2H]-2-phenylpropanoic acid
  参考文献：
  名称：

  Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂

  摘要：

  The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give alpha-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding alpha-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2).

  DOI：

  10.1021/ja3045053

文献信息

• FELBAMATE DERIVED COMPOUNDS
  申请人：University of Virginia Patent Foundation

  公开号：EP1282414A2

  公开（公告）日：2003-02-12
• [EN] FELBAMATE DERIVED COMPOUNDS<br/>[FR] COMPOSES DERIVES DE FELBAMATE
  申请人：UNIV VIRGINIA

  公开号：WO2001085149A2

  公开（公告）日：2001-11-15

  The invention relates to the use of certain felbamate derivatives to treat neuropathic pain, obesity, glaucoma, depression, and mood disorders, as well as other conditions.
• Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂
  作者：Mark D. Greenhalgh、Stephen P. Thomas

  DOI：10.1021/ja3045053

  日期：2012.7.25

  The iron-catalyzed hydrocarboxylation of aryl alkenes has been developed using a highly active bench-stable iron(II) precatalyst to give alpha-aryl carboxylic acids in excellent yields and with near-perfect regioselectivity. Using just 1 mol % FeCl2, bis(imino)pyridine 6 (1 mol %), CO2 (atmospheric pressure), and a hydride source (EtMgBr, 1.2 equiv), a range of sterically and electronically differentiated aryl alkenes were transformed to the corresponding alpha-aryl carboxylic acids (up to 96% isolated yield). The catalyst was found to be equally active with a loading of 0.1 mol %. Preliminary mechanistic investigations show that an iron-catalyzed hydrometalation is followed by transmetalation and reaction with the electrophile (CO2).