3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-(trifluoromethyl)-2H-1-benzopyran | 127486-51-5

• 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: 3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-(trifluoromethyl)-2H-1-benzopyran
• 英文别名: 3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-trifluoromethyl-2H-1-benzopyran；2,2-Dimethyl-6-(trifluoromethyl)-1a,7b-dihydrooxireno[2,3-c]chromene
• CAS: 127486-51-5
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: QKVOXJXJFVKWAI-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：

  3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-(trifluoromethyl)-2H-1-benzopyran 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-6-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：

  1-[(2-methylbut-3-yn-2-yl)oxy]-4-(trifluoromethyl)benzene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙醚 、 二甲基亚砜 、 邻二氯苯 为溶剂， 反应 1.0h， 生成 3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-(trifluoromethyl)-2H-1-benzopyran
  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 In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the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

• Compound and treatment
  申请人：Beecham Group p.l.c.

  公开号：US05254557A1

  公开（公告）日：1993-10-19

  A compound of formula (IA) in the form of a pharmaceutically acceptable microfine powder is disclosed. ##STR1##

  公开了以药用可接受的微细粉末形式的化合物（IA）的化学式。
• Chroman derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP0518342A1

  公开（公告）日：1992-12-16

  A chroman derivative represented by the following general formula [1]: wherein R₁ represents cyano group, nitro group, halogenomethyl group or -SO₂-X group (X represents lower alkyl group having 1-6 carbon atoms or aryl group); R₂ represents hydrogen atom or OA group (A represents hydrogen atom, nitro group, lower acyl group having 1-6 carbon atoms, arylcarbonyl group, lower alkylsulfonyl group having 1-6 carbon atoms, arylsulfonyl group, arylalkyl group, tetrahydropyranyl group, lower alkoxycarbonyl group having 1-6 carbon atoms, arylalkoxycarbonyl group or silyl derivative group); R₃ singly represents a hydrogen atom; or R₃ forms a bond jointly with R₂; and R₄, R₅, R₆ and R₇ each represent hydrogen atom, vinyl group, formyl group, -Y-(OA)n group (Y represents straight or branched chain alkylene group having 1-6 carbon atoms or lower alkenyl group having 1-6 carbon atoms, A is as defined above, and n represents an integer of 1-3, provided that when n is 2 or greater, each OA groups are identical or independent of one another) or -CO-Z group (Z represents hydrogen atom, lower alkyl group having 1-6 carbon atoms, aryl group, hydroxyl group or lower alkoxy group having 1-6 carbon atoms); provided that R₄, R₅, R₆ and R₇ are identical or independent of one another. The compound of this invention is expected to be effectively usable as an agent for prevention and treatment of various symptoms due to the contraction of smooth muscles, for prevention and treatment of the diseases of the circulatory system and for prevention and treatment of epilepsy.

  由以下通式[1]表示的铬烷衍生物： 其中 R₁ 代表氰基、硝基、卤代甲基或 -SO₂-X 基团（X 代表具有 1-6 个碳原子的低级烷基或芳基）；R₂ 代表氢原子或 OA 基团（A 代表氢原子、硝基、具有 1-6 个碳原子的低级酰基、芳基羰基、具有 1-6 个碳原子的低级烷基磺酰基、芳基磺酰基、芳烷基、四氢吡喃基、具有 1-6 个碳原子的低级烷氧基羰基、芳基烷氧基羰基或硅烷衍生物基团）；R₃ 单个代表氢原子；或 R₃ 与 R₂ 共同形成键；且 R₄、R₅、R₆ 和 R₇ 各自代表氢原子、乙烯基、甲酰基、-Y-(OA)n 基团（Y 代表具有 1-6 个碳原子的直链或支链亚烷基或具有 1-6 个碳原子的低级烯基，A 如上文所定义，且 n 代表 1-3 的整数）、但当 n 为 2 或更大时，每个 OA 基团彼此相同或独立）或-CO-Z 基团（Z 代表氢原子、具有 1-6 个碳原子的低级烷基、芳基、羟基或具有 1-6 个碳原子的低级烷氧基）；条件是 R₄、R₅、R₆ 和 R₇ 彼此相同或独立。 本发明的化合物有望有效地用作预防和治疗平滑肌收缩引起的各种症状、预防和治疗循环系统疾病以及预防和治疗癫痫的药物。
• BURRELL, GORDON;CASSIDY, FREDERICK;EVANS, JOHN M.;LIGHTOWLER, DIANE;STEMP+, J. MED. CHEM., 33,(1990) N1, C. 3023-3027
  作者：BURRELL, GORDON、CASSIDY, FREDERICK、EVANS, JOHN M.、LIGHTOWLER, DIANE、STEMP+

  DOI：——

  日期：——
• NOVEL COMPOUNDS AND TREATMENT
  申请人：BEECHAM GROUP PLC

  公开号：EP0373204A1

  公开（公告）日：1990-06-20
• US5254557A
  申请人：——

  公开号：US5254557A

  公开（公告）日：1993-10-19