3-<4,5-bis(benzyloxy)-2-fluorophenoxy>-1,2-epoxypropane | 132178-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-<4,5-bis(benzyloxy)-2-fluorophenoxy>-1,2-epoxypropane
• 英文别名: 2-([4,5-Bis(benzyloxy)-2-fluorophenoxy]methyl)oxirane；2-[[2-fluoro-4,5-bis(phenylmethoxy)phenoxy]methyl]oxirane
• CAS: 132178-23-5
• 化学式: C₂₃H₂₁FO₄
• 分子量: 380.416
• InChiKey: DSTAFKYVMGIONW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<4,5-bis(benzyloxy)-2-fluorophenoxy>-1,2-epoxypropane 在 palladium on activated charcoal 氢气 作用下， 反应 12.0h， 生成 3-(4,5-dihydroxy-2-fluorophenoxy)-3-(tert-butylamino)-2-propanol trifluoroacetate
  参考文献：
  名称：

  Effect of fluorine substitution on the adrenergic properties of 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol

  摘要：

  The 2- and 6-fluoro derivatives of the potent beta-adrenergic agonist 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol were prepared and their adrenergic properties examined. The order of potency was as follows: beta-adrenergic activity (simulation of cyclic AMP formation in C6 glioma cells), 2-F = parent >> 6-F; beta-1-activity (rate of contraction, guinea pig atria), parent > 2-F >> 6-F; beta-2-activity (relaxation of guinea pig tracheal strip), 2-F > parent >> 6-F. The affinity of the 2-fluoro analogue for beta-1-adrenergic receptors (inhibition of the specific binding of [H-3]dihydroalprenolol, rat cerebral cortical membranes) was 2 times greater, while the 6-fluoro analogue was 1450 times less than the parent. These results suggest that the aromatic rings of phenoxypropanolamine adrenergic agonists and phenylethanolamine adrenergic agonists bind in similar fashion to the adrenergic receptor, and that if interactions between fluorine and the side-chain hydroxyl group are critical in defining beta-adrenergic selectivity, the interactions are similar in both phenoxypropanolamines and phenylethanolamines.

  DOI：

  10.1021/jm00107a027
• 作为产物：
  描述：

  4,5-bis(benzyloxy)-2-fluorobenzaldehyde 在 氢氧化钾 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 46.0h， 生成 3-<4,5-bis(benzyloxy)-2-fluorophenoxy>-1,2-epoxypropane
  参考文献：
  名称：

  Effect of fluorine substitution on the adrenergic properties of 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol

  摘要：

  The 2- and 6-fluoro derivatives of the potent beta-adrenergic agonist 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol were prepared and their adrenergic properties examined. The order of potency was as follows: beta-adrenergic activity (simulation of cyclic AMP formation in C6 glioma cells), 2-F = parent >> 6-F; beta-1-activity (rate of contraction, guinea pig atria), parent > 2-F >> 6-F; beta-2-activity (relaxation of guinea pig tracheal strip), 2-F > parent >> 6-F. The affinity of the 2-fluoro analogue for beta-1-adrenergic receptors (inhibition of the specific binding of [H-3]dihydroalprenolol, rat cerebral cortical membranes) was 2 times greater, while the 6-fluoro analogue was 1450 times less than the parent. These results suggest that the aromatic rings of phenoxypropanolamine adrenergic agonists and phenylethanolamine adrenergic agonists bind in similar fashion to the adrenergic receptor, and that if interactions between fluorine and the side-chain hydroxyl group are critical in defining beta-adrenergic selectivity, the interactions are similar in both phenoxypropanolamines and phenylethanolamines.

  DOI：

  10.1021/jm00107a027

文献信息

• ADEJARE, ADEBOYE;NIE, JUN-YING;HEBEL, DAVID;BRACKETT, L. ELLEN;CHOI, OKSO+, J. MED. CHEM., 34,(1991) N, C. 1063-1068
  作者：ADEJARE, ADEBOYE、NIE, JUN-YING、HEBEL, DAVID、BRACKETT, L. ELLEN、CHOI, OKSO+

  DOI：——

  日期：——
• Effect of fluorine substitution on the adrenergic properties of 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol
  作者：Adeboye Adejare、Jun Ying Nie、David Hebel、L. Ellen Brackett、Oksoon Choi、Fabian Gusovsky、William L. Padgett、John W. Daly、Cyrus R. Creveling、Kenneth L. Kirk

  DOI：10.1021/jm00107a027

  日期：1991.3

  The 2- and 6-fluoro derivatives of the potent beta-adrenergic agonist 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol were prepared and their adrenergic properties examined. The order of potency was as follows: beta-adrenergic activity (simulation of cyclic AMP formation in C6 glioma cells), 2-F = parent >> 6-F; beta-1-activity (rate of contraction, guinea pig atria), parent > 2-F >> 6-F; beta-2-activity (relaxation of guinea pig tracheal strip), 2-F > parent >> 6-F. The affinity of the 2-fluoro analogue for beta-1-adrenergic receptors (inhibition of the specific binding of [H-3]dihydroalprenolol, rat cerebral cortical membranes) was 2 times greater, while the 6-fluoro analogue was 1450 times less than the parent. These results suggest that the aromatic rings of phenoxypropanolamine adrenergic agonists and phenylethanolamine adrenergic agonists bind in similar fashion to the adrenergic receptor, and that if interactions between fluorine and the side-chain hydroxyl group are critical in defining beta-adrenergic selectivity, the interactions are similar in both phenoxypropanolamines and phenylethanolamines.