2,4-二氯-3-苯基-喹啉 | 108832-15-1

• 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
• 中文名称: 2,4-二氯-3-苯基-喹啉
• 英文名称: 2,4-dichloro-3-phenylquinoline
• 英文别名: 2,4-dichloro-3-phenylquinolone；2,4-dichloro-3-phenyl-quinoline；2,4-Dichlor-3-phenyl-chinolin
• CAS: 108832-15-1
• 化学式: C₁₅H₉Cl₂N
• 分子量: 274.149
• InChiKey: AJFBGQFLYLZASL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2,4-二氯-3-苯基-喹啉 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到4-Azido-2-chloro-3-phenylquinoline
  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：

  3-苯基-4-羟基喹啉-2(1H)-酮 在 三氯氧磷 作用下， 生成 2,4-二氯-3-苯基-喹啉
  参考文献：
  名称：

  具有独立于溶剂和 pH 值的高荧光量子产率和发射最大值的 4-氰基-6,7-二甲氧基喹啉

  摘要：

  通过使用甲苯亚磺酸盐作为催化剂，从适当的 4-羟基喹诺酮 3 开始，通过反应性 4-氯喹诺酮 8，合成了高度荧光和稳定的 6,7-二甲氧基-2-氧喹啉-4-腈 (11)。与充分描述的 4-三氟甲基取代类似物 18 相比，N-取代衍生物 11 在水、极性和非极性溶剂中在 430-440 纳米的窄窗口中发出荧光，量子产率几乎恒定为 0.5。在 385 和 410 nm 之间的宽双最大值中可能产生相同的激发，在 pH 1 和 11 之间产生相同的数据。这些特性可能导致广泛使用的荧光标准。用溴乙酸酯进行 N-烷基化以良好的收率得到酯 13。反应性琥珀酰亚胺 (OSu) 酯 15 通过皂化为酸 14 制备。 与氨基酸或肽，在温和条件下，在弱碱性水性介质中实现与标记衍生物 17 的连接。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  DOI：

  10.1002/ejoc.200700855

文献信息

• 4-Cyano-6,7-dimethoxycarbostyrils with Solvent- and pH-Independent High Fluorescence Quantum Yields and Emission Maxima
  作者：Appasaheb B. Ahvale、Hana Prokopcová、Jana Šefčovičová、Waltraud Steinschifter、Anna E. Täubl、Georg Uray、Wolfgang Stadlbauer

  DOI：10.1002/ejoc.200700855

  日期：2008.1

  solvents in a narrow 430–440-nm window with almost constant quantum yield of 0.5. Equal excitation is possible in the broad double maximum between 385 and 410 nm yielding identical data between pH 1 and 11. These properties could lead to a broadly usable fluorescence standard. N-Alkylation with bromoacetate yields ester 13 in good yields. Reactive succinimidoyl (OSu) ester 15 was prepared by saponification

  通过使用甲苯亚磺酸盐作为催化剂，从适当的 4-羟基喹诺酮 3 开始，通过反应性 4-氯喹诺酮 8，合成了高度荧光和稳定的 6,7-二甲氧基-2-氧喹啉-4-腈 (11)。与充分描述的 4-三氟甲基取代类似物 18 相比，N-取代衍生物 11 在水、极性和非极性溶剂中在 430-440 纳米的窄窗口中发出荧光，量子产率几乎恒定为 0.5。在 385 和 410 nm 之间的宽双最大值中可能产生相同的激发，在 pH 1 和 11 之间产生相同的数据。这些特性可能导致广泛使用的荧光标准。用溴乙酸酯进行 N-烷基化以良好的收率得到酯 13。反应性琥珀酰亚胺 (OSu) 酯 15 通过皂化为酸 14 制备。 与氨基酸或肽，在温和条件下，在弱碱性水性介质中实现与标记衍生物 17 的连接。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany
• Substituted Quinoline Compounds For Use As Selective Estrogen Receptor Modulator
  申请人：Hoekstra Joel William

  公开号：US20070203180A1

  公开（公告）日：2007-08-30

  The present invention relates to novel compounds of formula (I) with a variety of therapeutic uses, more particularly novel substituted quinoline compounds particularly useful for selective estrogen receptor modulation.

  本发明涉及公式(I)的新化合物，具有多种治疗用途，更特别地，是新的取代喹啉化合物，特别适用于选择性雌激素受体调节。
• 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.
• DE547082
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs
  作者：Thomas P. Blackburn、Barry Cox、Allen J. Guildford、David J. Le Count、Derek N. Middlemiss、Robert J. Pearce、Craig W. Thornber

  DOI：10.1021/jm00395a013

  日期：1987.12

  A series of 2-[(2-aminoethyl)thio]quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists. The affinity of the compounds for 5-HT1 receptor sites was measured by their ability to displace [3H]-5-HT from rat brain synaptosomes whereas the affinity for 5-HT2 receptor sites was measured by their ability to displace [3H]spiperone from synaptosomes prepared from rat brain cortex. The 5-HT2 antagonist properties of the compounds were measured in vivo by their antagonism of 5-hydroxytryptophan-induced head twitches in the mouse and by their antagonism of hyperthermia induced by fenfluramine (N-ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochloride) in the rat. The structure-activity relationships in this series are discussed and the properties of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline hydrochloride (70) are highlighted.