3a-Hydroxy-8-methyl-1-(4-methylsulfanyl-phenyl)-4,5-dihydro-3aH-naphtho[2,1-b]furan-2-one | 503174-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3a-Hydroxy-8-methyl-1-(4-methylsulfanyl-phenyl)-4,5-dihydro-3aH-naphtho[2,1-b]furan-2-one
• 英文别名: 3a-hydroxy-8-methyl-1-(4-methylsulfanylphenyl)-4,5-dihydrobenzo[e][1]benzofuran-2-one
• CAS: 503174-38-7
• 化学式: C₂₀H₁₈O₃S
• 分子量: 338.427
• InChiKey: LIYDQWDBNPWLMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3a-Hydroxy-8-methyl-1-(4-methylsulfanyl-phenyl)-4,5-dihydro-3aH-naphtho[2,1-b]furan-2-one 在 Oxone 作用下， 以 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Conformationally restricted 3,4-diarylfuranones (2,3a,4,5-tetrahydronaphthofuranones) as selective cyclooxygenase-2 inhibitors

  摘要：

  A number of naphthofuranones were synthesized and tested for COX-1 and COX-2 inhibition. Few of them were identified as selective COX-2 inhibitors. Structure-activity relationship studies within the series are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00282-8
• 作为产物：
  描述：

  2-bromo-7-methyl-1,2,3,4-tetrahydronapthalin-1-one 在 氢氧化钾 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 3a-Hydroxy-8-methyl-1-(4-methylsulfanyl-phenyl)-4,5-dihydro-3aH-naphtho[2,1-b]furan-2-one
  参考文献：
  名称：

  Conformationally restricted 3,4-diarylfuranones (2,3a,4,5-tetrahydronaphthofuranones) as selective cyclooxygenase-2 inhibitors

  摘要：

  A number of naphthofuranones were synthesized and tested for COX-1 and COX-2 inhibition. Few of them were identified as selective COX-2 inhibitors. Structure-activity relationship studies within the series are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00282-8

文献信息

• A simple and rapid entry to 5-alkyl (aryl)-5-hydroxy-3,4-diarylfuranones and 3a-hydroxy-1-aryl-2,3a,4,5-tetrahydronaphthofuranones via a tandem esterification and oxidative cyclization process
  作者：Srinivas Padakanti、Venugopal Rao Veeramaneni、Vijaya Raghavan Pattabiraman、Manojit Pal、Koteswar Rao Yeleswarapu

  DOI：10.1016/s0040-4039(02)02144-5

  日期：2002.11

  A synthesis of 5-hydroxy-3,4-diarylfuranones and related derivatives is accomplished by the reaction of arylacetic acid with alpha-bromoketone in the presence of base and atmospheric oxygen. A variety of compounds were synthesized in good to excellent yield and many are of potential biological interest. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Conformationally restricted 3,4-diarylfuranones (2,3a,4,5-tetrahydronaphthofuranones) as selective cyclooxygenase-2 inhibitors
  作者：Manojit Pal、Venugopal Rao Veeramaneni、Murali Nagabelli、Srinivas Rao Kalleda、Parimal Misra、Seshagiri Rao Casturi、Koteswar Rao Yeleswarapu

  DOI：10.1016/s0960-894x(03)00282-8

  日期：2003.5

  A number of naphthofuranones were synthesized and tested for COX-1 and COX-2 inhibition. Few of them were identified as selective COX-2 inhibitors. Structure-activity relationship studies within the series are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.