3-benzyl-2,4-dichloroquinoline | 157027-28-6

• 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-benzyl-2,4-dichloroquinoline
• CAS: 157027-28-6
• 化学式: C₁₆H₁₁Cl₂N
• 分子量: 288.176
• InChiKey: QFLJAVIOPKFSLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzyl-2,4-dichloroquinoline 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.75h， 生成 N-(3-benzyl-2-chloroquinolin-4-yl)-1,1,1-triphenyl-l5-phosphanimine
  参考文献：
  名称：

  Regioselective Azidation of 2,4-Dichloroquinolines

  摘要：

  Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chloro-tetrazolo[1,5-a]quinolines (5g-i). When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines (5a-i) are obtained. Structural assignments of 3 and 5 have been carried out by C-13-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9). It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.

  DOI：

  10.1002/prac.19943360407
• 作为产物：
  描述：

  苄基丙二酸二乙酯 在 吡啶 、 三氯化铝 、 三氯氧磷 作用下， 以 氯苯 、 甲苯 为溶剂， 反应 22.5h， 生成 3-benzyl-2,4-dichloroquinoline
  参考文献：
  名称：

  Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines

  摘要：

  On the basis of the structure activity relationship (SAR) of 4-chloro-6-nitroquipazine (K-i = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (K-i = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [H-3]citalopram binding to the rat cortical membranes. Binding affinities of 3h and 4d were K-i = 2.70 +/- 0.32 and 2.23 +/- 0.46 nM. respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine. their in vitro binding affinitics. and the SAR of C3, C4 position in 6-nitroquipazine are described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.031

文献信息

• Reaction of Some 2-Quinolone Derivatives with Phosphoryl Chloride: Synthesis of Novel Phosphoric Acid Esters of 4-Hydroxy-2-quinolone
  作者：Ondřej Rudolf、Vladimír Mrkvička、Antonín Lyčka、Michal Rouchal、Antonín Klásek

  DOI：10.1002/jhet.1082

  日期：2013.2

  not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized

  3-氯喹啉-2,4-二酮不与磷酰氯反应，但是，在N，N-二甲基苯胺存在下会形成2,4-二氯喹啉和/或4-氯喹啉-2-酮。与这些化合物一起，分离出少量的4-羟基喹啉-2-酮的新型磷酸二氢酯。我们概述了一个简单的步骤，可以以中等到良好的产率制备这些化合物。所有化合物均通过1 H和13 C NMR，IR，EI-MS和ESI-MS光谱进行表征，在某些情况下通过31 P NMR光谱进行表征。
• Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines
  作者：Byung Seok Moon、Byoung Se Lee、Dae Yoon Chi

  DOI：10.1016/j.bmc.2005.05.031

  日期：2005.8

  On the basis of the structure activity relationship (SAR) of 4-chloro-6-nitroquipazine (K-i = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (K-i = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [H-3]citalopram binding to the rat cortical membranes. Binding affinities of 3h and 4d were K-i = 2.70 +/- 0.32 and 2.23 +/- 0.46 nM. respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine. their in vitro binding affinitics. and the SAR of C3, C4 position in 6-nitroquipazine are described. (c) 2005 Elsevier Ltd. All rights reserved.
• Regioselective Azidation of 2,4-Dichloroquinolines
  作者：Waltraud Steinschifter、Wolfgang Stadlbauer

  DOI：10.1002/prac.19943360407

  日期：——

  Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazolo[1,5-a]quinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chloro-tetrazolo[1,5-a]quinolines (5g-i). When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazolo[1,5-a]quinolines (5a-i) are obtained. Structural assignments of 3 and 5 have been carried out by C-13-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9). It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.