2,2-Dimethyl-7-trifluoromethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene | 136466-12-1

• 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: 2,2-Dimethyl-7-trifluoromethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene
• 英文别名: 2,2-Dimethyl-7-(trifluoromethyl)-1a,7b-dihydrooxireno[2,3-c]chromene；2,2-dimethyl-7-(trifluoromethyl)-1a,7b-dihydrooxireno[2,3-c]chromene
• CAS: 136466-12-1
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: JXKXQPWOBOYUCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-7-trifluoromethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 1-(2,2-Dimethyl-5-trifluoromethyl-2H-chromen-4-yl)-piperidin-2-one
  参考文献：
  名称：

  Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis

  摘要：

  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.

  DOI：

  10.1021/jm00173a019
• 作为产物：
  描述：

  间三氟甲基苯酚 在 potassium carbonate 、 间氯过氧苯甲酸 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 60.0h， 生成 2,2-Dimethyl-7-trifluoromethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene
  参考文献：
  名称：

  Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis

  摘要：

  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.

  DOI：

  10.1021/jm00173a019

文献信息

• [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.
• 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.