3-methoxy-4-hydroxy-5-fluorobenzyl cyanide | 104716-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-methoxy-4-hydroxy-5-fluorobenzyl cyanide
• 英文别名: 2-(3-Fluoro-4-hydroxy-5-methoxyphenyl)acetonitrile
• CAS: 104716-74-7
• 化学式: C₉H₈FNO₂
• 分子量: 181.166
• InChiKey: QMDQEVTZJMHZMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-hydroxy-5-fluorobenzyl cyanide 在 硼烷四氢呋喃络合物 、 三溴化硼 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 112.0h， 生成 N-[2-[3-fluoro-4,5-bis(phenylmethoxy)phenyl]ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide
  参考文献：
  名称：

  5-Fluoro- and 8-fluorotrimetoquinol: selective .beta.2-adrenoceptor agonists

  摘要：

  The 5-fluoro and 8-fluoro analogues of trimetoquinol, TMQ, have been synthesized and evaluated for beta 2- and beta 1-adrenoceptor activity in guinea pig trachea and atria, respectively. The fluoro analogues of TMQ maintained potent beta 2-adrenoceptor agonist activity but had reduced beta 1-adrenoceptor agonist activity. The changes in beta 1-activity of these compounds were correlated to differences in phenolic pKa's. The beta 1- and beta 2-adrenoceptor actions of 2 and 3 were blocked in a competitive manner by propranolol. The enhanced beta 2/beta 1 selectivity for the analogues was found to be 8-fluoro analogue 3 greater than 5-fluoro analogue 2 greater than trimetoquinol (1).

  DOI：

  10.1021/jm00384a015
• 作为产物：
  描述：

  2-氟-6-甲氧基苯酚 在 碘甲烷 作用下， 以 乙醇 、 水 为溶剂， 反应 27.0h， 生成 3-methoxy-4-hydroxy-5-fluorobenzyl cyanide
  参考文献：
  名称：

  5-Fluoro- and 8-fluorotrimetoquinol: selective .beta.2-adrenoceptor agonists

  摘要：

  The 5-fluoro and 8-fluoro analogues of trimetoquinol, TMQ, have been synthesized and evaluated for beta 2- and beta 1-adrenoceptor activity in guinea pig trachea and atria, respectively. The fluoro analogues of TMQ maintained potent beta 2-adrenoceptor agonist activity but had reduced beta 1-adrenoceptor agonist activity. The changes in beta 1-activity of these compounds were correlated to differences in phenolic pKa's. The beta 1- and beta 2-adrenoceptor actions of 2 and 3 were blocked in a competitive manner by propranolol. The enhanced beta 2/beta 1 selectivity for the analogues was found to be 8-fluoro analogue 3 greater than 5-fluoro analogue 2 greater than trimetoquinol (1).

  DOI：

  10.1021/jm00384a015

文献信息

• MILLER, DUANE D.;FELLER, DENNIS R.;CLARK, MICHAEL T.;ADEJARE, ADEBOYE;ROM+
  作者：MILLER, DUANE D.、FELLER, DENNIS R.、CLARK, MICHAEL T.、ADEJARE, ADEBOYE、ROM+

  DOI：——

  日期：——
• CLARK M. T.; ADEJARE A.; SHAMS G.; FELLER D. R.; MILLER D. D., J. MED. CHEM., 30,(1987) N 1, 86-90
  作者：CLARK M. T.、 ADEJARE A.、 SHAMS G.、 FELLER D. R.、 MILLER D. D.

  DOI：——

  日期：——
• MILLER, DUANE D.;FELLER, DENNIS R.;CLARK, MICHAEL T.
  作者：MILLER, DUANE D.、FELLER, DENNIS R.、CLARK, MICHAEL T.

  DOI：——

  日期：——
• 5-Fluoro- and 8-fluorotrimetoquinol: selective .beta.2-adrenoceptor agonists
  作者：Michael T. Clark、Adeboye Adejare、Gamal Shams、Dennis R. Feller、Duane D. Miller

  DOI：10.1021/jm00384a015

  日期：1987.1

  The 5-fluoro and 8-fluoro analogues of trimetoquinol, TMQ, have been synthesized and evaluated for beta 2- and beta 1-adrenoceptor activity in guinea pig trachea and atria, respectively. The fluoro analogues of TMQ maintained potent beta 2-adrenoceptor agonist activity but had reduced beta 1-adrenoceptor agonist activity. The changes in beta 1-activity of these compounds were correlated to differences in phenolic pKa's. The beta 1- and beta 2-adrenoceptor actions of 2 and 3 were blocked in a competitive manner by propranolol. The enhanced beta 2/beta 1 selectivity for the analogues was found to be 8-fluoro analogue 3 greater than 5-fluoro analogue 2 greater than trimetoquinol (1).