6-cyclohexyl-2,3-dihydro-5-methylbenzofuran-2-one | 60986-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-cyclohexyl-2,3-dihydro-5-methylbenzofuran-2-one
• 英文别名: 6-cyclohexyl-5-methyl-3H-1-benzofuran-2-one
• CAS: 60986-96-1
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: KVDBCJNAYVLNHC-UHFFFAOYSA-N

物化性质

• 沸点：
  378.2±42.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-环己基-2-甲氧基苯乙酮 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 水 、 氢气 、 三溴化硼 、 四氯化钛 、 对甲苯磺酸 、 sulfur 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 22.0~25.0 ℃ 、202.65 kPa 条件下， 反应 45.67h， 生成 6-cyclohexyl-2,3-dihydro-5-methylbenzofuran-2-one
  参考文献：
  名称：

  2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents

  摘要：

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.

  DOI：

  10.1021/jm00144a019

文献信息

• 2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents
  作者：Annemarie Closse、Walter Haefliger、Daniel Hauser、Hans Ulrich Gubler、Beatrice Dewald、Marco Baggiolini

  DOI：10.1021/jm00144a019

  日期：1981.12

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.