2,4-二氯-7-甲氧基-3-苯基喹啉 | 108832-16-2

• 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-7-甲氧基-3-苯基喹啉
• 英文名称: 2,4-dichloro-7-methoxy-3-phenyl-quinoline
• 英文别名: 2,4-dichloro-3-phenyl-7-methoxyquinoline；2,4-Dichloro-7-methoxy-3-phenylquinoline
• CAS: 108832-16-2
• 化学式: C₁₆H₁₁Cl₂NO
• 分子量: 304.175
• InChiKey: CFBPNDXUUDXHPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 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：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二氯-7-甲氧基-3-苯基喹啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-ethyl-3-phenyl-4-(4-bromophenyloxy)-7-methoxyquinoline
  参考文献：
  名称：

  Discovery of Novel Quinoline-Based Estrogen Receptor Ligands Using Peptide Interaction Profiling

  摘要：

  Traditional approaches to discovery of selective estrogen receptor modulators (SERMs) have relied on ER binding and cell-based estrogen response element-driven assays to identify compounds that are osteoprotective but nonproliferative in breast and uterine tissues. To discover new classes of potential SERMs, we have employed a cell-free microsphere-based binding assay to rapidly characterize ER alpha interactions with conformation-sensing cofactor or phage display peptides. Peptide profiles of constrained triarenes were compared to known proliferative and nonproliferative ER ligands to discover potent quinoline-based ligands with minimal Ishikawa cell stimulation.

  DOI：

  10.1021/jm040154f
• 作为产物：
  描述：

  4-羟基-7-甲氧基-3-苯基喹啉-2(1H)-酮 在 三氯氧磷 作用下， 反应 2.0h， 以91%的产率得到2,4-二氯-7-甲氧基-3-苯基喹啉
  参考文献：
  名称：

  [EN] SUBSTITUTED QUINOLINE COMPOUNDS FOR USE AS SELECTIVE ESTROGEN RECEPTOR MODULATOR
  [FR] COMPOSES QUINOLEINE SUBSTITUES A UTILISER EN TANT QUE MODULATEURS SELECTIFS DU RECEPTEUR DES OESTROGENES

  摘要：

  本发明涉及具有多种治疗用途的新型化合物（I）的配方，更具体地说是特别适用于选择性雌激素受体调节的新型取代喹啉化合物。

  公开号：

  WO2005082857A1

文献信息

• 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。
• 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.
• Potential non-steroidal estrogens and antiestrogens, IV Organic azides in heterocyclic synthesis, part 13: Synthesis of aza- and diazacoumestrols via azido derivatives
  作者：Wolfgang Stadlbauer、Rita Laschober、Thomas Kappe

  DOI：10.1007/bf00815924

  日期：1991.10

  4-Chloro-3-aryl-coumarins and quinolones 2 a-e undergo thermolytic ring closure by reaction with sodium azide in refluxing dimethyl formamide to yield indolo[3,2-c]coumarins and indolo[3,2-c]quinolin-6(5H)-ones 6 a-e. In the case of the coumarin 2 a the azido coumarin 5 can be isolated. The mono- and diazacoumestrol-dimethylethers 6 a-c are converted into the coumestrol analogues 7 a-c and their diacetyl derivatives 8 a-c.
• SUBSTITUTED QUINOLINE COMPOUNDS FOR USE AS SELECTIVE ESTROGEN RECEPTOR MODULATOR
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1727802A1

  公开（公告）日：2006-12-06
• US7405303B2
  申请人：——

  公开号：US7405303B2

  公开（公告）日：2008-07-29