N-[2-[3-fluoro-4,5-bis(phenylmethoxy)phenyl]ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide | 104716-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-[3-fluoro-4,5-bis(phenylmethoxy)phenyl]ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide
• CAS: 104716-80-5
• 化学式: C₃₃H₃₄FNO₆
• 分子量: 559.634
• InChiKey: MKCZQHPRHGVPLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  723.6±60.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[2-[3-fluoro-4,5-bis(phenylmethoxy)phenyl]ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 生成 8-fluoro-6,7-bis(phenylmethoxy)-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
  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：

  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

文献信息

• Markovich, Kimberly M.; Hamada, Akihiko; Miller, Duane D., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 6, p. 1665 - 1667
  作者：Markovich, Kimberly M.、Hamada, Akihiko、Miller, Duane D.

  DOI：——

  日期：——
• 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).