3-(3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester | 420786-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3-[(3-oxo-4H-1,4-benzoxazin-6-yl)oxymethyl]piperidine-1-carboxylate
• CAS: 420786-35-2
• 化学式: C₁₉H₂₆N₂O₅
• 分子量: 362.426
• InChiKey: JCMXYNRHUQKYCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 异丙醇 为溶剂， 反应 66.0h， 生成 6-{1-[2-(Quinolin-5-yloxy)-ethyl]-piperidin-3-ylmethoxy}-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity

  摘要：

  Starting from a high throughput screening hit, a series of 3,4-dihydro-2H-benzoxazinones has been identified with both high affinity for the 5-HT1A receptor and potent 5-HT reuptake inhibitory activity. The 5-(2-methyl)quinolinyloxy derivative combined high 5-HT1A/1B/1D receptor affinities with low intrinsic activity and potent inhibition of the 5-HT reuptake site (pK(i) 8.2). This compound also had good oral bioavailability and brain penetration in the rat. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.030
• 作为产物：
  描述：

  methyl [(4-hydroxy-2-nitrophenyl)oxy]acetate 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 20.0~50.0 ℃ 、300.0 kPa 条件下， 反应 36.0h， 生成 3-(3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity

  摘要：

  Starting from a high throughput screening hit, a series of 3,4-dihydro-2H-benzoxazinones has been identified with both high affinity for the 5-HT1A receptor and potent 5-HT reuptake inhibitory activity. The 5-(2-methyl)quinolinyloxy derivative combined high 5-HT1A/1B/1D receptor affinities with low intrinsic activity and potent inhibition of the 5-HT reuptake site (pK(i) 8.2). This compound also had good oral bioavailability and brain penetration in the rat. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.030