3-(4-Methoxycarbonylmethoxy-3-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 420786-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-Methoxycarbonylmethoxy-3-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 420786-27-2
• 化学式: C₁₉H₂₆N₂O₈
• 分子量: 410.424
• InChiKey: SZXIUTQYNSOMPL-UHFFFAOYSA-N

物化性质

• 沸点：
  539.6±35.0 °C(predicted)
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  117.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxycarbonylmethoxy-3-nitro-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 异丙醇 为溶剂， 50.0 ℃ 、300.0 kPa 条件下， 反应 84.0h， 生成 6-{1-[2-(Quinolin-5-yloxy)-ethyl]-pyrrolidin-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：

  benzoic acid 4-methoxycarbonylmethoxy-3-nitrophenyl ester 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 3-(4-Methoxycarbonylmethoxy-3-nitro-phenoxymethyl)-pyrrolidine-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