3-(3,5-di-tert-butyl-4-fluorophenyl)propanoic 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: 3-(3,5-di-tert-butyl-4-fluorophenyl)propanoic acid
• 英文别名: 3-(3,5-di-tert-butyl-4-fluoropheny)propanoic acid
• 化学式: C₁₇H₂₅FO₂
• 分子量: 280.383
• InChiKey: XAOZUAPXTWNERM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  对氟甲苯 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 硫酸 、 水 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 mineral oil 为溶剂， 反应 25.67h， 生成 3-(3,5-di-tert-butyl-4-fluorophenyl)propanoic acid
  参考文献：
  名称：

  Total Synthesis of a Reported Fluorometabolite from Streptomyces sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

  摘要：

  3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.

  DOI：

  10.1021/np500260z

文献信息

• Total Synthesis of a Reported Fluorometabolite from <i>Streptomyces</i> sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine
  作者：Mohammed Salah Ayoup、David B. Cordes、Alexandra M. Z. Slawin、David O’Hagan

  DOI：10.1021/np500260z

  日期：2014.6.27

  3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.