2-bromo-1-(3,4-dichlorophenyl)butan-1-one | 850352-47-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(3,4-dichlorophenyl)butan-1-one
• CAS: 850352-47-5
• 化学式: C₁₀H₉BrCl₂O
• 分子量: 295.991
• InChiKey: KZRPLFKVXPXPJR-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±32.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(3,4-dichlorophenyl)butan-1-one 、 叔丁胺 反应 15.0h， 以73%的产率得到2-(tert-butylamino)-3',4'-dichlorobutyrophenone
  参考文献：
  名称：

  [EN] MONOAMINE REUPTAKE INHIBITORS
  [FR] INHIBITEURS DE LA RECAPTURE DES MONOAMINES

  摘要：

  该发明提供了一种能够抑制一种或多种单胺再摄取的丁丙吡胺类似化合物。这些化合物可以选择性地结合到一种或多种单胺转运体上，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体。这些化合物可用于治疗对单胺再摄取抑制有响应的疾病，包括成瘾、抑郁和肥胖症。

  公开号：

  WO2010121022A1
• 作为产物：
  描述：

  3,4-二氯苯腈 在 三氯化铝 、 溴 作用下， 以 甲苯 为溶剂， 生成 2-bromo-1-(3,4-dichlorophenyl)butan-1-one
  参考文献：
  名称：

  1-（4-甲基苯基）-2-吡咯烷-1-基-戊基-1-酮（吡咯酮）类似物：一类有前途的单胺摄取抑制剂。

  摘要：

  多巴胺，5-羟色胺和去甲肾上腺素对于哺乳动物系统中的神经传递是必不可少的。这三种神经递质一直是大量研究的重点，因为它们的产生及其在单胺受体上的相互作用的调节对多种药理结果产生了深远的影响。我们的兴趣集中在寻找可卡因滥用药物的神经递质再摄取机制上。在本文中，我们描述了2-氨基戊苯酮阵列的合成和生物学评估。该阵列产生了多巴胺和去甲肾上腺素转运蛋白的选择性抑制剂，对5-羟色胺的转运几乎没有影响。化合物的子集对5HT1A，5HT1B，5HT1C，D1，D2或D3受体没有明显的亲和力。铅化合物外消旋的1-（4-甲基苯基）-2-吡咯烷-1-基-戊基-1-一4a，将其拆分成对映异构体，发现S异构体是最具生物活性的对映异构体。在这些DAT / NET选择性化合物中，最有效的化合物是1-（3,4-二氯苯基）-（4u）和1-萘基-（4t）2-吡咯烷基-1-基戊基-1-酮类似物。

  DOI：

  10.1021/jm050797a

文献信息

• Unexpected Role of <i>p</i>-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
  作者：Jiajia Chen、Wei Guo、Zhenrong Wang、Lin Hu、Fan Chen、Yuanzhi Xia

  DOI：10.1021/acs.joc.6b00844

  日期：2016.7.1

  The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration

  的反应p -toluenesulfonylmethyl胩（TOSMIC）用α-溴代化合物有效地导致α-磺化酮，酯和酰胺的报道，其中TOSMIC作为磺酰化剂的显式的新角色被揭露首次。通过对照实验和DFT计算进行的机理研究表明，该反应是由Cu（OTf）2催化的TOSMIC水合引发的，形成了甲酰胺中间体，该中间体在Cs 2 CO 3添加剂的介导下易于进行C-S键裂解。
• Pyrovalerone Analogues and Therapeutic Uses Thereof
  申请人：Butler David

  公开号：US20080234498A1

  公开（公告）日：2008-09-25

  New compounds that bind to monoamine transporters are described. The compounds of the present invention can be racemic or pure R— or S-enantiomers. Certain preferred compounds of the present invention have a high selectively dopamine transporter versus the serotonin transporter. Preferred monoamine transporters for the practice of the present invention include the dopamine transporter, the serotonin transporter and the norepinephrine transporter.

  本发明描述了结合到单胺转运体的新化合物。本发明的化合物可以是外消旋或纯的R-或S-对映体。本发明的某些优选化合物具有高选择性的多巴胺转运体与血清素转运体。本发明实施的优选单胺转运体包括多巴胺转运体、血清素转运体和去甲肾上腺素转运体。
• MONOAMINE REUPTAKE INHIBITORS
  申请人：Carroll Frank Ivy

  公开号：US20120071560A1

  公开（公告）日：2012-03-22

  The invention provides bupropion analogue compounds capable of inhibiting the reuptake of one or more monoamines. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin. Such compounds may be used to treat conditions that are responsive to inhibition of the reuptake of monoamines, including addiction, depression, and obesity.

  本发明提供了能够抑制一种或多种单胺再摄取的伯泊隆类似化合物。该化合物可以选择性地结合到一种或多种单胺转运体上，包括多巴胺、去甲肾上腺素和血清素。这种化合物可用于治疗对单胺再摄取抑制有反应的疾病，包括成瘾、抑郁和肥胖症。
• Monoamine reuptake inhibitors
  申请人：Research Triangle Institute

  公开号：US10919841B2

  公开（公告）日：2021-02-16

  The invention provides bupropion analogue compounds capable of inhibiting the reuptake of one or more monoamines. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin. Such compounds may be used to treat conditions that are responsive to inhibition of the reuptake of monoamines, including addiction, depression, and obesity.

  本发明提供了能够抑制一种或多种单胺再摄取的安非他酮类似物化合物。这些化合物可选择性地与一种或多种单胺转运体结合，包括多巴胺、去甲肾上腺素和血清素的转运体。此类化合物可用于治疗对抑制单胺再摄取有反应的病症，包括成瘾、抑郁症和肥胖症。
• Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction
  作者：F. Ivy Carroll、Bruce E. Blough、Philip Abraham、Andrew C. Mills、J. Ashley Holleman、Scott A. Wolckenhauer、Ann M. Decker、Antonio Landavazo、K. Timothy McElroy、Hernán A. Navarro、Michael B. Gatch、Michael J. Forster

  DOI：10.1021/jm901189z

  日期：2009.11.12

  A series of bupropion (1a) analogues (1b-1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a la analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [H-3]dopamine ([H-3]DA), [H-3]serotonin ([H-3](HT)-H-5), and [H-3]norepinephrine ([H-3]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [I-125]RTI-55 in cloned transporters. Several analogues showed increased [H-3]DA uptake inhibition with reduced or little change in [H-3](HT)-H-5 and [H-3]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a tithe course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.