7-chloro-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol | 1597548-45-2

• 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: 7-chloro-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol
• CAS: 1597548-45-2
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: JBCMGHYDIBPOQV-UHFFFAOYSA-N

物化性质

• 沸点：
  298.5±40.0 °C(predicted)
• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5,7-dichloro-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol 在 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 5-chloro-3,3-dimethyl-2,3-dihydrobenzofuran-4-ol 、 7-chloro-3,3-dimethyl-2,3-dihydrobenzofuran-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