trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-(trifluoromethyl)-2H-1-benzopyran-4-ol | 130219-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-(trifluoromethyl)-2H-1-benzopyran-4-ol
• 英文别名: (3R,4S)-3-bromo-2,2-dimethyl-6-(trifluoromethyl)-3,4-dihydrochromen-4-ol
• CAS: 130219-68-0；136466-16-5
• 化学式: C₁₂H₁₂BrF₃O₂
• 分子量: 325.125
• InChiKey: ZGFSQXKVJYIGKM-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-(trifluoromethyl)-2H-1-benzopyran-4-ol 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 生成 1-((3R,4S)-3-Hydroxy-2,2-dimethyl-6-trifluoromethyl-chroman-4-yl)-pyrrolidin-2-one
  参考文献：
  名称：

  Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.

  DOI：

  10.1021/jm00173a018
• 作为产物：
  描述：

  对三氟甲基苯酚 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 水 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 邻二氯苯 为溶剂， 反应 1.0h， 生成 trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-(trifluoromethyl)-2H-1-benzopyran-4-ol
  参考文献：
  名称：

  Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.

  DOI：

  10.1021/jm00173a018

文献信息

• Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis
  作者：Derek R. Buckle、Jonathon R. S. Arch、Ashley E. Fenwick、Catherine S. V. Houge-Frydrych、Ivan L. Pinto、David G. Smith、Stephen G. Taylor、John M. Tedder

  DOI：10.1021/jm00173a019

  日期：1990.11

  A series of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans related to the potassium channel activator cromakalim have been prepared and evaluated for their relaxant activity in guinea pig isolated tracheal spirals. Several analogues show enhanced relaxant activity relative to cromakalim in this preparation and the rank order of potency for those substituents investigated at C-6 was CF3 greater than CN greater than C2H5 greater than aza greater than or equal to CH3. One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel activators is stereoselective.
• [EN] TRIFLUOROMETHYL SUBSTITUTED COMPOUNDS AND A PHARMACEUTICAL COMPOSITION
  申请人：BEECHAM GROUP PLC

  公开号：WO1991009031A1

  公开（公告）日：1991-06-27

  (EN) A compound of formula (I) or, where appropriate, a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein A1, A2, A3, A4, R1, R2, R3, R4 and Y are as defined herein; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compound and composition in medicine.(FR) Composé ayant la formule (I) ou, dans les cas appropriés, un de ses sels ou un de ses solvates pharmaceutiquement acceptables. Dans la formule (I), A1, A2, A3, A4, R1, R2, R3, R4 et Y ont la définition décrite. Procédé de préparation de ce composé, composition pharmaceutique contenant ce composé, utilisation de ce composé et de cette composition en médecine.