1-(4-溴苯基)-3-(4-氯苯基)-1-丙酮 | 296271-45-9

• 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
• 中文名称: 1-(4-溴苯基)-3-(4-氯苯基)-1-丙酮
• 英文名称: 1-(4-bromophenyl)-3-(4-chlorophenyl)propan-1-one
• 英文别名: 4'-Bromo-3-(4-chlorophenyl)propiophenone
• CAS: 296271-45-9
• 化学式: C₁₅H₁₂BrClO
• 分子量: 323.617
• InChiKey: AAQWRXMBFZVSIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1-(4-溴苯基)-3-(4-氯苯基)-1-丙酮 在 sodium acetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 2-[3-(4-bromophenyl)-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-(4-chlorobenzylidene)-1,3-thiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis, characterization, and biological evaluation of certain 1,3-thiazolone derivatives bearing pyrazoline moiety as potential anti-breast cancer agents

  摘要：

  A series of 5-arylidene-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-1,3-thiazol-4(5H)-ones were synthesized and screened for their in vitro antitumor activity against human breast adenocarcinoma cell line (MCF-7). Five of the test compounds exhibited good antitumor activity superior to the reference drug, doxorubicin, with IC50 range 1.4-2.3 mu M. Among the test compounds, 2-[3,5-bis(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-5-(2-methoxybenzylidene)-1,3-thiazol-4(5H)-one (3i) was found to show the most potent anticancer activity.

  DOI：

  10.1007/s00044-012-0098-7
• 作为产物：
  描述：

  1-(4-溴苯基)-3-(4-氯苯基)-2-丙烯-1-酮 在 tris(triphenylphosphine)ruthenium(II) chloride 、 乙二醇 作用下， 反应 5.0h， 生成 1-(4-溴苯基)-3-(4-氯苯基)-1-丙酮
  参考文献：
  名称：

  Homogeneous RuCl₂(PPh₃)₃-Catalyzed Regioselective Liquid-Phase Transfer Hydrogenation of Carbon−Carbon Double Bond in Chlorobenzylidene Ketones with Ethylene Glycol as Hydrogen Donor

  摘要：

  The regioselective transfer hydrogenation of a carbon-carbon double bond of different chlorobenzylidene ketones is effectuated in ethylene glycol with a very high selectivity in the presence of homogeneous, tris(triphenylphosphine)ruthenium-(II) chloride catalyst. Different important process parameters such as temperature, catalyst loading, and reaction period are studied. The reaction follows a first order kinetics, and the energy of activation was found to be 52 kJ/mol.

  DOI：

  10.1021/op0000327

文献信息

• Designed pincer ligand supported Co(<scp>ii</scp>)-based catalysts for dehydrogenative activation of alcohols: Studies on <i>N</i>-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
  作者：Anshu Singh、Ankur Maji、Mayank Joshi、Angshuman R. Choudhury、Kaushik Ghosh

  DOI：10.1039/d0dt03748f

  日期：——

  Base-metal catalysts Co1, Co2 and Co3 were synthesized from designed pincer ligands L1, L2 and L3 having NNN donor atoms respectively. Co1, Co2 and Co3 were characterized by IR, UV–Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures of Co1 and Co3. Catalysts Co1, Co2 and Co3 were utilized to study the dehydrogenative

  贱金属催化剂Co1、Co2和Co3由分别具有NNN供体原子的设计的钳状配体L 1、L 2和L 3合成。Co1、Co2和Co3通过 IR、UV-Vis 进行表征。和 ESI-MS 光谱研究。研究了单晶 X 射线衍射研究以验证Co1和Co3的分子结构。催化剂Co1 , Co2和Co3用于研究醇的脱氢活化胺的N-烷基化、酮的 α-烷基化和喹啉的合成。在优化的反应条件下，开发了广泛的底物，包括醇类、苯胺类和酮类。对胺的N-烷基化、酮的 α-烷基化和喹啉合成的一系列控制实验进行了检查，以了解反应途径。研究了 ESI-MS 光谱研究以表征钴-醇盐和钴-氢化物中间体。研究了反应过程中放出的氢气对苯乙烯的还原，以验证催化剂的脱氢性质。为N提出了可能的反应途径-胺类烷基化、酮类α-烷基化和喹啉的合成基于对照实验和反应中间体的检测。
• Efficient Organoruthenium Catalysts for α‐Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines <i>via</i> Hydrogen Borrowing Strategy and their Mechanistic Studies
  作者：Ankur Maji、Anshu Singh、Neetu Singh、Kaushik Ghosh

  DOI：10.1002/cctc.202000254

  日期：2020.6.5

  for C−C bond formation and exhibited excellent performance in the dehydrogenative coupling of ketones and amides. In the synthesis of C–C bonds, alcohols were utilized as the alkylating agent. A broad range of substrates, including sterically hindered ketones and alcohols, were well tolerated under the optimized conditions (TON up to 47000 and TOF up to 11750 h−1). This ruthenium (II) catalysts were

  一个新的无膦有机金属钌（II）催化剂家族（Ru1 - Ru4），由二齿NN Schiff碱配体（L 1 -L 4，其中L 1 = N，N-二甲基-4-（（2-苯基-2- （吡啶-2-基甲基）肼基）甲基）苯胺，L 2 = N，N-二乙基-4-（（2-苯基-2-（甲基-2-基甲基）肼基）甲基）苯胺，L 3 = N， N-2-甲基-4-（（2-苯基-2-（吡啶-2-基）肼基亚甲基）甲基）苯胺和L 4= N，N-二乙基-4-（（2-苯基-2-（吡啶-2-基）肼基亚甲基）甲基）苯胺被制备并表征。这些半三明治配合物可作为C-C键形成的催化剂，在酮和酰胺的脱氢偶联中表现出出色的性能。在CC键的合成中，醇被用作烷基化剂。在最佳条件下（TON高达47000，TOF高达11750 h -1），各种各样的底物，包括位阻酮和醇，都具有良好的耐受性。该钌（II）催化剂对o的脱氢环化也具有活性-氨基苄醇，用于形成喹啉
• BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions
  作者：Zhaojun Xu、Xiaoli Yu、Xinxin Sang、Dawei Wang

  DOI：10.1039/c8gc00557e

  日期：——

  A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient and green borrowing hydrogen reaction and dehydrogenative cyclization. This BINAP-Cu complex supported by hydrotalcite is highly air-stable and can be recycled at least five times under solvent-free conditions. Notably, 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives could

  已经开发了由水滑石支撑的BINAP-Cu系统，并被证明是一种高效的催化剂，用于原子效率高的绿色借入氢反应和脱氢环化反应。这种由水滑石负载的BINAP-Cu络合物具有高度的空气稳定性，在无溶剂条件下可以循环至少五次。值得注意的是，第一次以水为溶剂仅一步即可由醇合成1-苄基-2-芳基-1 H-苯并[ d ]咪唑衍生物。这为在水或无溶剂条件下以高收率合成官能化的胺，酮和1-苄基-2-芳基-1 H-苯并[ d ]咪唑衍生物提供了一种更加绿色有效的催化方法。
• SmI ₂ ‐mediated C‐alkylation of Ketones with Alcohols under Microwave Conditions: A Novel Route to Alkylated Ketones
  作者：Gaurav Pawar、Shaik Mahammad Ghouse、Swayamsiddha Kar、Sai Manohar Chelli、Srinivas Reddy Dannarm、Jitendra Gour、Rajesh Sonti、Srinivas Nanduri

  DOI：10.1002/asia.202200041

  日期：2022.4.14

  A microwave-assisted SmI2-catalysed protocol has been developed for the direct C-alkylation of ketones with alcohols. The developed methodology showed diverse substrate scope with good functional group tolerance. The methodology is also useful for the synthesis of substituted quinolines via Friedländer reaction. The synthetic applicability of the reaction is well explored by preparation of Donepezil

  已经开发了一种微波辅助SmI 2催化方案，用于酮与醇的直接 C-烷基化。所开发的方法显示出多种底物范围，具有良好的官能团耐受性。该方法还可用于通过 Friedländer 反应合成取代的喹啉。通过多奈哌齐的制备和孕烯醇酮的功能化，很好地探索了该反应的合成适用性。进行从头算 DFT 研究以验证似是而非的机制。
• Fe ₃ O ₄ @CS‐Ni: An efficient and recyclable magnetic nanocatalyst for <i>α</i> ‐alkylation of ketones with benzyl alcohols by borrowing hydrogen methodology
  作者：Mina Taheri‐Torbati、Hossein Eshghi

  DOI：10.1002/aoc.6838

  日期：2022.10

  heterogeneous magnetic impressive nickel catalyst in which Fe3O4 nanoparticles have been coated with chitosan and decorated with nickel nanoparticles (Fe3O4@CS-Ni). This catalyst has been used for direct α-alkylation of aryl ketones with substituted benzyl alcohols through borrowing hydrogen and dehydrogenation mechanism that affords the corresponding α-benzyl ketones, with good to excellent yield. The

  本文报道了一种非均相磁性镍催化剂，其中 Fe 3 O 4纳米粒子已涂有壳聚糖并用镍纳米粒子（Fe 3 O 4 @CS-Ni）进行装饰。该催化剂通过借氢和脱氢机理用于芳基酮与取代苯甲醇的直接α-烷基化反应，得到相应的α-苄基酮，具有良好至极好的收率。核壳形态已通过不同的分析技术进行确认，例如傅里叶变换红外 (FT-IR)、X 射线衍射 (XRD)、振动样品磁力计 (VSM)、扫描电子显微镜 (SEM)、透射电子显微镜 ( TEM)、SEM 映射、能量色散 X 射线 (EDX)、电感耦合等离子体 (ICP) 和热重分析 (TGA)。此外，催化剂可以通过使用外部磁场从反应混合物中回收并重复使用六个连续循环，而催化活性不会显着降低。