benzyl N-benzenesulfonyl-3-bromo-4-(4-isopropoxyphenyl)pyrrole-2-carboxylate | 1426329-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: benzyl N-benzenesulfonyl-3-bromo-4-(4-isopropoxyphenyl)pyrrole-2-carboxylate
• 英文别名: Benzyl 1-(benzenesulfonyl)-3-bromo-4-(4-propan-2-yloxyphenyl)pyrrole-2-carboxylate；benzyl 1-(benzenesulfonyl)-3-bromo-4-(4-propan-2-yloxyphenyl)pyrrole-2-carboxylate
• CAS: 1426329-89-6
• 化学式: C₂₇H₂₄BrNO₅S
• 分子量: 554.461
• InChiKey: BFXXWEXGXUOWNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-benzenesulfonyl-3-bromo-4-(4-isopropoxyphenyl)pyrrole-2-carboxylate 在 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 benzyl 4-(4-isopropoxyphenyl)-3-(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]pyrrole-2-carboxylate
  参考文献：
  名称：

  Total synthesis of the marine natural products lukianols A and B

  摘要：

  Total synthesis of the pyrrolic marine natural products lukianols A (1) and B (2) has been achieved using N-benzenesulfonyl-3,4-dibromopyrrole (3) as a common starting material. The key synthetic strategy developed is the combined bromine-directed lithiation and palladium-catalyzed cross-coupling of 3 to produce 3,4-diarylpyrrol-2-carboxylates. Regioselective iodination of the phenolic intermediate 24 was thoroughly investigated for the synthesis of lukianol B. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.01.077
• 作为产物：
  描述：

  4-异丙氧基苯硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 16.0h， 生成 benzyl N-benzenesulfonyl-3-bromo-4-(4-isopropoxyphenyl)pyrrole-2-carboxylate
  参考文献：
  名称：

  Total synthesis of the marine natural products lukianols A and B

  摘要：

  Total synthesis of the pyrrolic marine natural products lukianols A (1) and B (2) has been achieved using N-benzenesulfonyl-3,4-dibromopyrrole (3) as a common starting material. The key synthetic strategy developed is the combined bromine-directed lithiation and palladium-catalyzed cross-coupling of 3 to produce 3,4-diarylpyrrol-2-carboxylates. Regioselective iodination of the phenolic intermediate 24 was thoroughly investigated for the synthesis of lukianol B. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.01.077

文献信息

• Total synthesis of the marine natural products lukianols A and B
  作者：Kaoru Takamura、Hisami Matsuo、Ayana Tanaka、Junji Tanaka、Tsutomu Fukuda、Fumito Ishibashi、Masatomo Iwao

  DOI：10.1016/j.tet.2013.01.077

  日期：2013.4

  Total synthesis of the pyrrolic marine natural products lukianols A (1) and B (2) has been achieved using N-benzenesulfonyl-3,4-dibromopyrrole (3) as a common starting material. The key synthetic strategy developed is the combined bromine-directed lithiation and palladium-catalyzed cross-coupling of 3 to produce 3,4-diarylpyrrol-2-carboxylates. Regioselective iodination of the phenolic intermediate 24 was thoroughly investigated for the synthesis of lukianol B. (C) 2013 Published by Elsevier Ltd.