7,8-bis(4-isopropoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one | 1426329-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7,8-bis(4-isopropoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one
• 英文别名: 3-(4-Methoxyphenyl)-7,8-bis(4-propan-2-yloxyphenyl)pyrrolo[2,1-c][1,4]oxazin-1-one；3-(4-methoxyphenyl)-7,8-bis(4-propan-2-yloxyphenyl)pyrrolo[2,1-c][1,4]oxazin-1-one
• CAS: 1426329-86-3
• 化学式: C₃₂H₃₁NO₅
• 分子量: 509.602
• InChiKey: XIMCILQOCXWFKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,8-bis(4-isopropoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以100%的产率得到lukianol A
  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：

  benzyl 3,4-bis(4-isopropoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]pyrrole-2-carboxylate 在 palladium on carbon 、 氢气 、 sodium acetate 作用下， 以 乙酸酐 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 7,8-bis(4-isopropoxyphenyl)-3-(4-methoxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one
  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.