8-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-5H-benzo[f][1,4]oxazepine-4-carboxylic acid tert-butyl ester | 1361110-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 8-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-5H-benzo[f][1,4]oxazepine-4-carboxylic acid tert-butyl ester
• 英文别名: tert-Butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate；tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,5-dihydro-2H-1,4-benzoxazepine-4-carboxylate
• CAS: 1361110-65-7
• 化学式: C₂₀H₃₀BNO₅
• 分子量: 375.273
• InChiKey: AZYLRHPNPQAURO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-chloro-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-8-carbonitrile 、 8-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-5H-benzo[f][1,4]oxazepine-4-carboxylic acid tert-butyl ester 在 四(三苯基膦)钯 、 碳酸氢钠 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 1.17h， 生成 7-(2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-8-yl)-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-8-carbonitrile
  参考文献：
  名称：

  Imidazo[1,2-a]pyridines: Orally Active Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor

  摘要：

  Advanced leads of an imidazopyridine series of positive allosteric modulators of the metabotropic glutamate 2 (mGlu2) receptor are reported. The optimization of in vitro ADMET and in vivo pharmacokinetic properties led to the identification of 27o. With good potency and selectivity for the mGlu2 receptor, 270 affected sleep-wake architecture in rats after oral treatment, which we have previously shown to be indicative of mGlu2 receptor-mediated central activity.

  DOI：

  10.1021/jm201561r
• 作为产物：
  描述：

  tert-butyl 8-bromo-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以70%的产率得到8-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-5H-benzo[f][1,4]oxazepine-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Imidazo[1,2-a]pyridines: Orally Active Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor

  摘要：

  Advanced leads of an imidazopyridine series of positive allosteric modulators of the metabotropic glutamate 2 (mGlu2) receptor are reported. The optimization of in vitro ADMET and in vivo pharmacokinetic properties led to the identification of 27o. With good potency and selectivity for the mGlu2 receptor, 270 affected sleep-wake architecture in rats after oral treatment, which we have previously shown to be indicative of mGlu2 receptor-mediated central activity.

  DOI：

  10.1021/jm201561r

文献信息

• Imidazo[1,2-<i>a</i>]pyridines: Orally Active Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor
  作者：Andrés A. Trabanco、Gary Tresadern、Gregor J. Macdonald、Juan Antonio Vega、Ana Isabel de Lucas、Encarnación Matesanz、Aránzazu García、María Lourdes Linares、Sergio A. Alonso de Diego、José Manuel Alonso、Daniel Oehlrich、Abdelah Ahnaou、Wilhelmus Drinkenburg、Claire Mackie、José Ignacio Andrés、Hilde Lavreysen、José María Cid

  DOI：10.1021/jm201561r

  日期：2012.3.22

  Advanced leads of an imidazopyridine series of positive allosteric modulators of the metabotropic glutamate 2 (mGlu2) receptor are reported. The optimization of in vitro ADMET and in vivo pharmacokinetic properties led to the identification of 27o. With good potency and selectivity for the mGlu2 receptor, 270 affected sleep-wake architecture in rats after oral treatment, which we have previously shown to be indicative of mGlu2 receptor-mediated central activity.