1-phenyl-3-(2-chloro-3,4-dimethoxyphenyl)-2-propen-1-one | 399031-84-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-phenyl-3-(2-chloro-3,4-dimethoxyphenyl)-2-propen-1-one
• 英文别名: 3-(2-chloro-3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 399031-84-6
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: DQWGTHJLGHCRJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(2-chloro-3,4-dimethoxyphenyl)-2-propen-1-one 在 二氮烯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以79.8%的产率得到5-(2-chloro-3,4-dimethoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines

  摘要：

  Ten new 3,5-diphenyl-2-pyrazoline derivatives were synthesised by reacting 1,3-diphenyl-2-propen-1-one with hydrazine hydrate. The chemical structures of the compounds were proved by means of their IR, H-1-NMR spectroscopic data and microanalyses. The antidepressant activities of these compounds were evaluated by the 'Porsolt Behavioural Despair Test' on Swiss-Webster mice. 3-(4-Methoxyphenyl)-5-(3,4-dimethoxyphenyl)-2-pyrazoline, 3-(4-methoxyphenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-pyrazoline and 3-(4-chlorophenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-pyrazoline reduced 41.94-48.62% immobility times at 100 mg kg(-1) dose level. In addition, it was found that 4-methoxy and 4-chloro substituents on the phenyl ring at position 3 of the pyrazoline ring increased the antidepressant activity; the replacement of these groups by bromo and methyl substituents decreased activity in mice. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01243-0
• 作为产物：
  描述：

  2-氯-3,4-二甲氧基苯甲醛 、 苯乙酮 生成 1-phenyl-3-(2-chloro-3,4-dimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  1-硫代氨基甲酰基-3,5-二苯基-4,5-二氢-1H-吡唑衍生物的合成及单胺氧化酶抑制活性

  摘要：

  十新1-硫代氨基甲酰基-3-(苯基和/或4-取代苯基)-5-(3,4-二甲氧基苯基和/或2-氯-3,4-二甲氧基苯基)-4,5-二氢-1H-吡唑衍生物是通过 1,3-diphenylpropen-1-ones 和氨基硫脲反应合成的。通过IR、1H-NMR、ESI-MS光谱数据和元素分析验证了化合物的化学结构。通过体外试验研究了所有化合物选择性抑制单胺氧化酶 (MAO) 的能力。从大鼠肝脏匀浆和人血小板的线粒体提取物中分离和纯化单胺氧化酶。将化合物的单胺氧化酶抑制活性与帕吉林和氯吉林进行比较。大多数化合物抑制大鼠肝脏匀浆的总活性。1-硫代氨基甲酰基-3-(4-甲氧基苯基)-5-(3,4-二甲氧基苯基)-4,5-二氢-1H-吡唑和1-硫代氨基甲酰基-3-(4-甲氧基苯基)对单胺氧化酶-A的抑制作用) -5- (2-氯-3,4-二甲氧基苯基) -4,5-二氢-1H-吡唑被检测到与氯吉林一样有效。合成化合物对大鼠肝脏单胺氧化酶-A

  DOI：

  10.1002/ardp.200700159

文献信息

• Regioselective Synthesis of 3-Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides
  作者：Jumreang Tummatorn、Piyapratch Poonsilp、Phongprapan Nimnual、Jindaporn Janprasit、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1021/acs.joc.5b00375

  日期：2015.5.1

  Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4 + 2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method could also be applied to other quinoline derivatives using appropriate alkynes. Moreover, the current strategy could be utilized for the diastereoselective synthesis of tetrahydroquinoline derivatives employing alkenyl

  3-溴喹啉衍生物的区域选择性合成是通过由芳基甲基叠氮化物生成的N-芳基亚胺离子与1-溴代炔烃之间进行正式的[4 + 2]-环加成反应而实现的。使用适当的炔烃，该方法也可应用于其他喹啉衍生物。而且，当前的策略可以用于以良好或优异的收率使用烯基底物的非对映选择性合成四氢喹啉衍生物。
• Synthesis and antidepressant activities of some 1,3,5-triphenyl-2-pyrazolines
  作者：E Palaska、D Erol、R Demirdamar

  DOI：10.1016/s0223-5234(96)80005-5

  日期：1996.1

  Ten new 1,3,5-triphenyl-2-pyrazoline derivatives were synthesized by reacting 1,3-diphenyl-2-propen-1-one with phenylhydrazine. The chemical structures of the compounds were proved by means of their UV, IR, H-1-NMR spectroscopic data and elementary analyses. The antidepressant activities of these compounds were screened by the Porsolt behavioral despair test. 1-Phenyl-3-(4-methylphenyl)-5-(3,4-dimethoxyphenyl)-2-pyrazoline and 1-phenyl-3-(4-methylphenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-prazoline showed significant antidepressant activity compared with clomipramine and tranylcypromine. A methyl substituent on the phenyl ring at position 3 of the pyrazoline ring enhances the antidepressant activity; the replacement of this methyl group by chloro or bromo substituents decreases the activity. In addition, introduction of a chloro substituent to the phenyl at the position 5 decreases the antidepressant activity.