3-(2-bromoethoxy)quinoline | 143102-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(2-bromoethoxy)quinoline
• CAS: 143102-09-4
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: DYCYHHRGBMDIFI-UHFFFAOYSA-N

物化性质

• 沸点：
  362.2±22.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethoxy)quinoline 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以86%的产率得到3-(2-bromoethoxy)quinoline 1-oxide
  参考文献：
  名称：

  Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part 1.

  摘要：

  3-(2-Bromoethyltosylamino)quinoline 1-oxide (4) reacted with TsCl-NH4OH and TsCl-K2CO3 to afford the 2-aminoquinoline (5) and the 2-quinolinone (8). Cyclization of 5 and 8 under basic conditions gave the piperazino-quinoline (6) and the morpholino-quinoline (9). Similar reactions of 3-(2-bromoethoxy)quinoline 1-oxide (13) in the presence of TsCl gave also the 2-aminoquinoline (14) and the 2-hydroxyquinoline (16), but accompanied with fair amounts of by-products (15 and, 15 and 17). Cyclization of 14 and 16 gave the morpholino-quinoline (18) and the 1,4-dioxano-quinoline (19) in somewhat lower yields.

  DOI：

  10.3987/com-92-5999
• 作为产物：
  描述：

  3-羟基喹啉 、 1,2-二溴乙烷 在 caesium carbonate 、 4-甲基-2-戊酮 作用下， 生成 3-(2-bromoethoxy)quinoline
  参考文献：
  名称：

  Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113474

文献信息

• Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part III. Intramolecular Cyclization of Quinoline 1-Oxides Bearing Active Methylene Groups at the 3-Position in the Presence of Acetic Anhydride
  作者：Yutaka Miura、Yasuo Fujimura、Sakae Takaku、Masatomo Hamana

  DOI：10.3987/com-92-s(t)131

  日期：——

  3-N-Alkylcyanoacetamidoquinoline 1-oxides (3a and 3c) react with Ac2O at room temperature in chloroform to afford 1-alkyl-3-cyano-4H-pyrrolo[3,2-b]quinolin-2-ones (4a and 4c). The cyclization of 3-N-alkylethoxycarbonylacetamidoquinoline 1-oxides (3b and 3d) occurs upon heating with Ac2O at 60-degrees-C. 3-(3,3-Dicyanopropoxy) quinoline 1-oxide (5) also cyclizes to the pyranoquinoline (6) when treated with Ac2O at room temperature in chloroform-DMF.
• A comparison of the binding of three series of nicotinic ligands
  作者：Mase Lee、Malgorzata Dukat、Liang Liao、Dwight Flammia、M. Imad Damaj、Billy Martin、Richard A. Glennon

  DOI：10.1016/s0960-894x(02)00298-6

  日期：2002.8

  A total of 24 aryl-substituted analogues of nicotine (1a) and two related series of nicotinic ligands, aminomethylpyridines 3 and ether analogues 8, were examined to determine if they bind at alpha4beta2 nACh receptors in a common manner. A modest correlation (r = 0.785) was found between the affinities of the nicotine analogues and derivatives of 3, but little correlation (r = 0.348) was found with analogues 8. However, a modest correlation (r = 0.742) exists between the binding of analogues 3 and 8. It seems that 1-series and 8-series compounds bind differently but that the 3-series compounds share some intermediate binding similarity with both. (C) 2002 Published by Elsevier Science Ltd.