7-bromo-3,3-dimethyl-2H-1-benzofuran-4-ol | 1624613-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 7-bromo-3,3-dimethyl-2H-1-benzofuran-4-ol
• CAS: 1624613-35-9
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: XSYNRCKEBKBQLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,6-二氯间苯二酚 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol 、 7-bromo-3,3-dimethyl-2H-1-benzofuran-4-ol
  参考文献：
  名称：

  A Scalable Route to an Unusual 3,3-Dimethyl-2,3-dihydrobenzofuran Ring System Present in an HCV Drug Candidate

  摘要：

  A scalable synthesis of a key intermediate used for the preparation of an HCV inhibitor containing an unusual dimethyldihydrobenzofuran ring is described. A key element for the successful completion of the synthesis was the correct ordering of a sequence of bromination, chlorination, and methylation to provide optimized selectivity and improved yield. A tin hydride-mediated ring closure was replaced with a more environmentally benign sulfuric acid-catalyzed Friedel-Crafts reaction. The overall yield for the preparation of the key intermediate was increased from less than 5 to 40%.

  DOI：

  10.1021/op4003467

文献信息

• [EN] HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS<br/>[FR] DÉRIVÉS D'HYDANTOÏNE UTILES COMME INHIBITEURS DE KV3
  申请人：AUTIFONY THERAPEUTICS LTD

  公开号：WO2013083994A1

  公开（公告）日：2013-06-13

  The invention provides compounds of formula (I): Said compounds being modulators of Kv3 channels and of use in the prophylaxis or treatment of related disorders.

  该发明提供了化合物的公式(I)：所述化合物是Kv3通道的调节剂，并用于预防或治疗相关疾病。
• HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS
  申请人：Autifony Therapeutics Limited

  公开号：EP2788339A1

  公开（公告）日：2014-10-15
• A Scalable Route to an Unusual 3,3-Dimethyl-2,3-dihydrobenzofuran Ring System Present in an HCV Drug Candidate
  作者：Ping Wang、Andrew J. Briggs

  DOI：10.1021/op4003467

  日期：2014.5.16

  A scalable synthesis of a key intermediate used for the preparation of an HCV inhibitor containing an unusual dimethyldihydrobenzofuran ring is described. A key element for the successful completion of the synthesis was the correct ordering of a sequence of bromination, chlorination, and methylation to provide optimized selectivity and improved yield. A tin hydride-mediated ring closure was replaced with a more environmentally benign sulfuric acid-catalyzed Friedel-Crafts reaction. The overall yield for the preparation of the key intermediate was increased from less than 5 to 40%.