methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate | 920752-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate
• 英文别名: Methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate；methyl 6,7,8-tribromo-2H-chromene-5-carboxylate
• CAS: 920752-15-4
• 化学式: C₁₁H₇Br₃O₃
• 分子量: 426.887
• InChiKey: XFCMLLGVFCRFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate 在 palladium diacetate 、 copper diacetate 、 氧气 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 methyl 5,6,7-tribromo-2-methyl-benzofuran-4-carboxylate 、 methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate
  参考文献：
  名称：

  Synthesis of tribromobenzofuran and tribromobenzopyran derivatives from methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate

  摘要：

  Palladium(II)-catalyzed oxidative cyclization of methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate 4 gave a mixture of methyl 5,6,7-tribromo-2-methyl-benzofuran-4-carboxylate 5 and methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate 6; the ratio of the two products varied between 71:29 and 24:76 depending on the reaction conditions. On the other hand, NBS or NIS mediated cyclization of 4 followed by treatment with NaOMe or DBU furnished benzofuran derivative 5 in good overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.005

文献信息

• Synthesis of tribromobenzofuran and tribromobenzopyran derivatives from methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate
  作者：Faiz Ahmed Khan、Laxminarayana Soma

  DOI：10.1016/j.tetlet.2006.11.005

  日期：2007.1

  Palladium(II)-catalyzed oxidative cyclization of methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate 4 gave a mixture of methyl 5,6,7-tribromo-2-methyl-benzofuran-4-carboxylate 5 and methyl 6,7,8-tribromo-2H-1-benzopyran-5-carboxylate 6; the ratio of the two products varied between 71:29 and 24:76 depending on the reaction conditions. On the other hand, NBS or NIS mediated cyclization of 4 followed by treatment with NaOMe or DBU furnished benzofuran derivative 5 in good overall yield. (c) 2006 Elsevier Ltd. All rights reserved.