(E)-1-(3-bromophenyl)-3-(p-tolyl)prop-2-en-1-one | 851581-65-2

• 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: (E)-1-(3-bromophenyl)-3-(p-tolyl)prop-2-en-1-one
• 英文别名: (2E)-1-(3-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one；(E)-1-(3-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 851581-65-2
• 化学式: C₁₆H₁₃BrO
• 分子量: 301.183
• InChiKey: SSFBIJVHFIFWPE-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-bromophenyl)-3-(p-tolyl)prop-2-en-1-one 在 sodium methylate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.2h， 生成 3-[4-(3-bromophenyl)-6-p-tolyl-pyrimidin-2-yl]-2-(4-chlorophenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Microwave Irradiated Synthesis of Pyrimidine Containing, Thiazolidin-4- ones: Antimicrobial, Anti-Tuberculosis, Antimalarial and Anti-Protozoa Evaluation

  摘要：

  目的： 本研究旨在合成带有嘧啶核的噻唑烷-4-酮化合物，并对不同种类的细菌、真菌、原虫和疟原虫进行评估。 背景： 微波辐射是合成噻唑烷-4-酮环系的最佳方法。合成噻唑烷-4-酮只需15分钟，而传统方法需要12小时。快速反应是本研究的主要关注点。 方法： 使用微波辐射合成2-(4-氯苯基)-3-(4-(取代苯基)-6-(取代芳基)嘧啶-2-基)噻唑烷-4-酮(6A-J)，以节省能源和时间。通过光谱分析(1H NMR、13C NMR、IR、光谱)确定所有新合成的结构，并对大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌和链球菌的抗菌活性、对白色念珠菌、黑曲霉和鼠伤寒杆菌的抗真菌活性、对结核分枝杆菌H37RV的抗结核活性、对疟原虫的抗疟疾活性以及对L.mexicana和T. cruzi的抗原虫活性进行筛选。 结果： 由于微波辐射合成，制备新化合物的时间很短。化合物6B、6C、6D、6E、6G、6H和6J的生物反应非常好。 结论： 使用微波辐射在较短的时间内获得了高产率和纯度的新合成噻唑烷-4-酮化合物。该系列化合物中的一些化合物的生物反应非常好。

  DOI：

  10.2174/1570178619666220111124104
• 作为产物：
  描述：

  Alpha-甲基苯乙烯 、 2-(3-溴苯基)-2-氧代乙酸 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 sodium acetate 、 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以70%的产率得到(E)-1-(3-bromophenyl)-3-(p-tolyl)prop-2-en-1-one
  参考文献：
  名称：

  多米诺-氟化-原脱氟可通过光氧化还原催化实现α-氧代羧酸与苯乙烯的脱羧交叉偶联

  摘要：

  通过光氧化还原催化，已经开发出α-酮酸与苯乙烯的多米诺氟化-原脱氟脱羧交叉偶联。该策略的关键部分是通过捕获以碳为中心的自由基中间体形成碳-氟（C-F）键，这将克服苯乙烯自由基官能化过程中的副反应。实验研究提供了证据，表明具有α-酮酸的多米诺氟化-原脱氟途径可引发光氧化还原循环。本催化方案还提供了在温和条件下构建α，β-不饱和酮的新方法。

  DOI：

  10.1021/acs.joc.7b01054

文献信息

• [EN] PYRIDINE COMPOUNDS AS INHIBITORS OF DIPEPTIDYL PEPTIDASE IV<br/>[FR] COMPOSES PYRIDINES UTILISES COMME INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005042488A1

  公开（公告）日：2005-05-12

  A compound represented by the formula wherein R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R3 is an optionally substituted aromatic group; R4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式表示为其中R1和R2相同或不同，每个都是可选择取代的碳氢基团或可选择取代的羟基团；R3是可选择取代的芳香基团；R4是可选择取代的氨基团；L是二价链状碳氢基团；Q是键或二价链状碳氢基团；X是氢原子、氰基、硝基、酰基、取代的羟基团、可选择取代的硫醇基团、可选择取代的氨基团或可选择取代的环状基团；但当X是乙氧羰基团时，Q为二价链状碳氢基团。该化合物具有肽酶抑制作用，可用作糖尿病等疾病的预防或治疗药物，并在功效、作用持续时间、特异性、毒性较低等方面具有优越性。
• Benzannulation of 3-Substituted Pyrroles to Indoles
  作者：Alan R. Katritzky、Stephane Ledoux、Satheesh K. Nair

  DOI：10.1021/jo026853m

  日期：2003.7.1

  In a new general indole synthesis, the anion derived from benzotriazolyl derivative 5b underwent regioselective 1,4-addition to various alpha,beta-unsaturated ketones; subsequent acid-catalyzed cyclization formed the corresponding indoles 1a-f.

  在新的一般吲哚合成中，衍生自苯并三唑基衍生物5b的阴离子在各种α，β-不饱和酮上进行了区域选择性的1,4-加成。随后酸催化的环化反应形成相应的吲哚1a-f。
• Pyridine compounds as inhibitors of dipeptidyl peptidase IV
  申请人：Oi Satoru

  公开号：US20070037807A1

  公开（公告）日：2007-02-15

  A compound represented by the formula wherein R 1 and R 2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted hydroxy group; R 3 is an optionally substituted aromatic group; R 4 is an optionally substituted amino group; L is a divalent chain hydrocarbon group; Q is a bond or a divalent chain hydrocarbon group; and X is a hydrogen atom, a cyano group, a nitro group, an acyl group, a substituted hydroxy group, an optionally substituted thiol group, an optionally substituted amino group or an optionally substituted cyclic group; provided that when X is an ethoxycarbonyl group, then Q is a divalent chain hydrocarbon group. The compound has a peptidase inhibitory action, is useful as an agent for the prophylaxis or treatment of diabetes and the like, and is superior in efficacy, duration of action, specificity, lower toxicity and the like.

  该化合物的化学式为其中R1和R2是相同或不同的可选择取代的烃基或可选择取代的羟基；R3是可选择取代的芳香基；R4是可选择取代的氨基；L是二价链烃基；Q是键或二价链烃基；X是氢原子、氰基、硝基、酰基、可选择取代的羟基、可选择取代的硫醇基、可选择取代的氨基或可选择取代的环状基；但当X是乙氧羰基时，Q是二价链烃基。该化合物具有肽酶抑制作用，可用作预防或治疗糖尿病等药物，具有优异的疗效、持续时间、特异性、低毒性等特点。
• Syntheses and evaluation of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline derivatives
  作者：Asha Budakoti、Abdul R. Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.026

  日期：2008.8

  A variety of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline were obtained by the refluxing of 1-N-thiocarbamoyl 3,5-diphenyl-2-pyrazoline with 2,3-dichloroquinoxaline. The chemical structures of the compounds were elucidated by UV, IR, H-1 NMR, and C-13 NMR spectroscopy. The purity of the compounds was confirmed by their elemental analysis. The antiamoebic activity of these compounds was evaluated by microdilution method against HMI:IMSS strain of Entamoeba histolytica and the IC50 values were compared with the standard drug metronidazole. Some of the quinoxaline derivatives showed less IC50 values than metronidazole. To elucidate the toxic effect, MTT assay was performed using kidney epithelial cell line. The results showed that all the compounds are non-toxic. (c) 2007 Elsevier Masson SAS. All rights reserved.
• A general and efficient Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones
  作者：T.M. Rangarajan、Kavita Devi、Akhilesh K. Verma、Rishi Pal Singh、Raj Pal Singh

  DOI：10.1016/j.jfluchem.2016.04.013

  日期：2016.6

  An efficient unprecedented Pd-catalyzed rapid 2-fluoroethoxylation of bromo-chalcones has been unveiled. The oxygen nucleophiles (fluoroalcohols) experience the rapid C-O bond forming reaction for the first time, albeit the alcohols are known to be a weak nucleophile and have greater competing beta-hydride elimination in the transition-metal-catalyzed (especially Pd and Cu) C-O cross-coupling reaction. The higher fluoroalcohols have also been effectively coupled with bromo-chalcones with relatively lower rate. (C) 2016 Elsevier B.V. All rights reserved.