methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate | 920752-13-2

• 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: methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate
• 英文别名: Methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate；methyl 2,3,4-tribromo-5-hydroxy-6-prop-2-enylbenzoate
• CAS: 920752-13-2
• 化学式: C₁₁H₉Br₃O₃
• 分子量: 428.903
• InChiKey: NBAIJSOZDBAGPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到4-Benzofurancarboxylic acid,5,6,7-tribromo-2-(bromomethyl)-2,3-dihydro-, methyl ester
  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
• 作为产物：
  描述：

  5-Allyloxy-2,3,4-tribromo-benzoic acid methyl ester 以 xylene 为溶剂， 反应 45.0h， 以89%的产率得到methyl 2-allyl-4,5,6-tribromo-3-hydroxybenzoate
  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.