(4aS,10bR)-1,5,5-trimethyl-2-oxo-4a,10b-dihydrochromeno[3,4-b][1,4]oxazine-9-carbonitrile | 205312-21-6

• 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: (4aS,10bR)-1,5,5-trimethyl-2-oxo-4a,10b-dihydrochromeno[3,4-b][1,4]oxazine-9-carbonitrile
• CAS: 205312-21-6
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: SWYCOTBCUBZYLG-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aS,10bR)-1,5,5-trimethyl-2-oxo-4a,10b-dihydrochromeno[3,4-b][1,4]oxazine-9-carbonitrile 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到(4aS,10bS)-1,5,5-trimethyl-2-oxo-4a,10b-dihydrochromeno[3,4-b][1,4]oxazine-9-carbonitrile
  参考文献：
  名称：

  Synthesis of 2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers

  摘要：

  A series of optically active tetrahydro-oxazino[2,3-c]benzopyran derivatives have been synthesized and evaluated for potassium channel opening activity. (4aR,11bR)-1-Benzoyl-5,5-dimethyl-2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitrile ((-)-11e) was identified as a bladder-selective potassium channel opener (IC50,bladder = 8.15 mu M, IC50,portal vein = 34.5 mu M). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00046-8
• 作为产物：
  描述：

  (3S-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (4aS,10bR)-1,5,5-trimethyl-2-oxo-4a,10b-dihydrochromeno[3,4-b][1,4]oxazine-9-carbonitrile
  参考文献：
  名称：

  Synthesis of 2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers

  摘要：

  A series of optically active tetrahydro-oxazino[2,3-c]benzopyran derivatives have been synthesized and evaluated for potassium channel opening activity. (4aR,11bR)-1-Benzoyl-5,5-dimethyl-2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitrile ((-)-11e) was identified as a bladder-selective potassium channel opener (IC50,bladder = 8.15 mu M, IC50,portal vein = 34.5 mu M). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00046-8

文献信息

• Wolf; Weiss-Greiler; Wolschann, Pharmazie, 1996, vol. 51, # 11, p. 836 - 839
  作者：Wolf、Weiss-Greiler、Wolschann、Ecker、Fleischhacker

  DOI：——

  日期：——
• Synthesis of 2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers
  作者：Chen-Yu Cheng、Hsin-I Chiu、Ming-Jyh Chang、Yen-Chung Lin、Ming-Cheng Tsai、Hon-Cheng Yu

  DOI：10.1016/s0960-894x(98)00046-8

  日期：1998.3

  A series of optically active tetrahydro-oxazino[2,3-c]benzopyran derivatives have been synthesized and evaluated for potassium channel opening activity. (4aR,11bR)-1-Benzoyl-5,5-dimethyl-2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitrile ((-)-11e) was identified as a bladder-selective potassium channel opener (IC50,bladder = 8.15 mu M, IC50,portal vein = 34.5 mu M). (C) 1998 Elsevier Science Ltd. All rights reserved.