2-Bromo-2-(4-fluorophenyl)propanoic acid | 72191-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Bromo-2-(4-fluorophenyl)propanoic acid
• CAS: 72191-41-4
• 化学式: C₉H₈BrFO₂
• 分子量: 247.064
• InChiKey: LMNLHAFFIHWFRU-UHFFFAOYSA-N

物化性质

• 沸点：
  295.9±25.0 °C(Predicted)
• 密度：
  1.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromo-2-(4-fluorophenyl)propanoic acid 、 甲基磺酰氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成
  参考文献：
  名称：

  Stereospecific Decarboxylative Allylation of Sulfones

  摘要：

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.

  DOI：

  10.1021/ja104196x
• 作为产物：
  描述：

  2-(4-氟苯基)-2-羟基丙酸 在 potassium carbonate 、 bromide acetone 作用下， 生成 2-Bromo-2-(4-fluorophenyl)propanoic acid
  参考文献：
  名称：

  Stereospecific Decarboxylative Allylation of Sulfones

  摘要：

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.

  DOI：

  10.1021/ja104196x

文献信息

• US4349683A
  申请人：——

  公开号：US4349683A

  公开（公告）日：1982-09-14
• Stereospecific Decarboxylative Allylation of Sulfones
  作者：Jimmie D. Weaver、Being J. Ka、David K. Morris、Ward Thompson、Jon A. Tunge

  DOI：10.1021/ja104196x

  日期：2010.9.8

  Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.