4-(2,2,2-trichloroethoxysulfonyloxy)benzoic acid benzyl ester | 653605-32-4

• 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: 4-(2,2,2-trichloroethoxysulfonyloxy)benzoic acid benzyl ester
• 英文别名: benzyl 4-(2,2,2-trichloroethoxysulfonyloxy)benzoate；Benzoic acid, 4-[[(2,2,2-trichloroethoxy)sulfonyl]oxy]-, phenylmethyl ester
• CAS: 653605-32-4
• 化学式: C₁₆H₁₃Cl₃O₆S
• 分子量: 439.701
• InChiKey: ZQEAPSHBGVRYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2,2,2-trichloroethoxysulfonyloxy)benzoic acid benzyl ester 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以81%的产率得到4-sulfooxybenzoic acid diammonium salt
  参考文献：
  名称：

  Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety

  摘要：

  [GRAPHICS]The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.

  DOI：

  10.1021/ol036157o
• 作为产物：
  描述：

  溴甲苯 在 4-二甲氨基吡啶 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 21.5h， 生成 4-(2,2,2-trichloroethoxysulfonyloxy)benzoic acid benzyl ester
  参考文献：
  名称：

  Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids

  摘要：

  Epidemiological studies indicate that flavonoid intake is inversely associated with the risk of coronary heart disease, yet the mechanisms responsible for their bioactivity are still a matter of debate. Based on the rapid and extensive metabolism of most flavonoids, their health effects most likely result from the biological activity of their metabolites. However, a lack of commercially available compounds/standards has prevented the study of metabolite bioactivity and resulted in a focus on non-physiologically relevant precursor/parent structures. This paper details the synthesis of a series of phenolic glucuronide 1a-e and sulfate 2a-e derivates as candidate metabolites for use as reference compounds in metabolic profiling studies and for the exploration of flavonoid bioactivity. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.03.100

文献信息

• Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety
  作者：Yong Liu、I-Feh Felicia Lien、Scott Ruttgaizer、Peter Dove、Scott D. Taylor

  DOI：10.1021/ol036157o

  日期：2004.1.1

  [GRAPHICS]The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.
• Flavonoid metabolism: the synthesis of phenolic glucuronides and sulfates as candidate metabolites for bioactivity studies of dietary flavonoids
  作者：Qingzhi Zhang、K. Saki Raheem、Nigel P. Botting、Alexandra M.Z. Slawin、Colin D. Kay、David O'Hagan

  DOI：10.1016/j.tet.2012.03.100

  日期：2012.6

  Epidemiological studies indicate that flavonoid intake is inversely associated with the risk of coronary heart disease, yet the mechanisms responsible for their bioactivity are still a matter of debate. Based on the rapid and extensive metabolism of most flavonoids, their health effects most likely result from the biological activity of their metabolites. However, a lack of commercially available compounds/standards has prevented the study of metabolite bioactivity and resulted in a focus on non-physiologically relevant precursor/parent structures. This paper details the synthesis of a series of phenolic glucuronide 1a-e and sulfate 2a-e derivates as candidate metabolites for use as reference compounds in metabolic profiling studies and for the exploration of flavonoid bioactivity. (C) 2012 Published by Elsevier Ltd.