3-Anilino-1-<4-brom-phenyl>-prop-2-enon | 3711-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Anilino-1-<4-brom-phenyl>-prop-2-enon
• 英文别名: 3-anilino-1-(4-bromo-phenyl)-propenone；3-Anilino-1-(4-brom-phenyl)-propenon；4-Brom-ω-anilinomethylen-acetophenon；4-Brom-β-phenylimino-propiophenon；(2E)-1-(4-bromophenyl)-3-(phenylamino)prop-2-en-1-one；3-anilino-1-(4-bromophenyl)prop-2-en-1-one
• CAS: 3711-70-4
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: RNSSCYNXZVOAEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Anilino-1-<4-brom-phenyl>-prop-2-enon 在 对甲苯磺酰叠氮 、 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65 mg的产率得到1-phenyl-4-(4-bromophenoyl)-1,2,3-triazole
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975
• 作为产物：
  描述：

  1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 、 苯胺 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3-Anilino-1-<4-brom-phenyl>-prop-2-enon
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975

文献信息

• One-Pot Methylenation–Cyclization Employing Two Molecules of CO₂ with Arylamines and Enaminones
  作者：Yulei Zhao、Xu Liu、Lijun Zheng、Yulan Du、Xinrui Shi、Yunlin Liu、Zhengquan Yan、Jinmao You、Yuanye Jiang

  DOI：10.1021/acs.joc.9b02858

  日期：2020.1.17

  7-triazabicyclo[4.4.0]dec-5-ene and ZnCl2-catalyzed procedure was characterized by the selective conversion of two molecules of CO2 into methylene groups in a multicomponent cyclization reaction. According to the computational study and control experiments, the reaction might proceed through the generation of bis(silyl)acetal and condensation of arylamine and aza-Diels-Alder processes. Moreover, the resulting

  首次讨论了使用两个带有烯胺酮和伯芳香胺的CO2分子进行的一锅甲基化环化反应，首次获得了环化产物。这种1,5,7-三氮杂双环[4.4.0] dec-5-ene和ZnCl2催化的过程的特征是，在多组分环化反应中，将两个分子的CO2选择性转化为亚甲基。根据计算研究和对照实验，该反应可能通过双（甲硅烷基）乙缩醛的生成以及芳基胺和氮杂-Diels-Alder方法的缩合进行。此外，所得产品可能是具有可调节光物理性质的潜在有机构件。
• Highly Regioselective Synthesis of Multisubstituted Pyrroles via Ag-Catalyzed [4+1C]^insert Cascade
  作者：Kaixiu Luo、Shuai Mao、Kun He、Xianglin Yu、Junhong Pan、Jun Lin、Zhihui Shao、Yi Jin

  DOI：10.1021/acscatal.9b05360

  日期：2020.3.20

  C–C bond carbenoid formal insertion/cyclization/[1,5]-shift cascade reaction was successfully developed, providing distinct chemo- and regioselective multisubstituted pyrroles. The plausible reaction mechanism involves two catalytic cycles: in the first one, silver ions regioselectively catalyze the C–C bond formal insertion reaction; in the second one, silver ions chemo- and regioselectively control

  成功开发了一种有效的[4 + 1C]插入方法，通过AgOTf催化的C–C键类胡萝卜素正式插入/环化/ [1,5]-移位级联反应将烯胺酮与供体/受体或供体/供体碳烯偶联。提供不同的化学和区域选择性多取代吡咯。可能的反应机理涉及两个催化循环：在第一个催化循环中，银离子区域选择性催化C–C键形式插入反应；在第二个中，银离子化学和区域选择性地控制环化和[1,5]转移反应。该方法不仅为多取代吡咯的合成提供了便利，并在多价吡咯的合成中应用了原子经济性，而且为通过简便修饰所得4 H进一步实现吡咯多样化提供了切入点。-吡咯产物，如天然产物lamellarin L的简短形式合成所示。
• Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones
  作者：Yulin Sun、Zhuoyuan Liu、Donghan Liu、Mingshuai Zhang、Longkun Chen、Zhangmengjie Chai、Xue-Bing Chen、Fuchao Yu

  DOI：10.1021/acs.joc.3c00925

  日期：2023.8.18

  functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)–H bond functionalization/C(sp3)–O bond cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction of 1,4-DHPs by using esters as the C4 sources, as well as expands the application

  通过铁(II)介导的氧化自由基级联C(sp 3 )–H键功能化/C(sp 3 )从环醚和烯胺酮合成高度官能化的4-烷基化1,4-二氢吡啶(1,4-DHP )首次开发了-O键断裂/环化反应。这种新颖的合成策略为以酯类为C4源构建1,4-DHPs提供了一种替代方法，并扩展了醚类在杂环合成中的应用。
• An Oxidative [3+2+1] Cyclization of Enaminones and N‐Alkenyl‐2‐pyrrolidinone: Access to Polysubstituted 4‐Alkylated 1,4‐dihydropyridines
  作者：Zhangmengjie Chai、Longkun Chen、Zhuoyuan Liu、Yulin Sun、Donghan Liu、Mingshuai Zhang、Yongchao Wang、Fuchao Yu

  DOI：10.1002/adsc.202300088

  日期：——

  4-alkylated 1,4-dihydropyridines (1,4-DHPs). By using terminal olefin as the C4 source of the 1,4-DHP skeleton, this synthetic strategy provides a series of 1,4-DHPs through a 1,1-difunctionalization/cyclization process. In this protocol, two C(sp3)−C(sp2) bonds and a C(sp2)−N bond are simultaneously formed, the hydrogen source on the newly formed methyl group of the 1,4-DHP skeleton is confirmed and a possible

  烯胺酮和N -烯基-2-吡咯烷酮的氧化 [3+2+1] 环化用于合成 4-烷基化 1,4-二氢吡啶 (1,4-DHP)。通过使用末端烯烃作为 1,4-DHP 骨架的 C4 来源，该合成策略通过 1,1-双官能化/环化过程提供了一系列 1,4-DHP。在该方案中，两个C( sp 3 )−C( sp 2 )键和一个C( sp 2 )−N键同时形成，确认了1,4-DHP骨架新形成的甲基上的氢源并提出了一种可能的机制。
• Fe-mediated oxidative cascade [1 + 2 + 3]-cyclization/esterification reaction: synthesis of 4-alkylated 1,4-dihydropyridines
  作者：Zhuoyuan Liu、Yulin Sun、Mingshuai Zhang、Longkun Chen、Xue-Bing Chen、Xiang Li、Fuchao Yu

  DOI：10.1039/d3ob00704a

  日期：——

  An Fe-mediated four-component reaction of enaminones, anhydrides and tetrahydrofuran through a cascade [1 + 2 + 3]-cyclization/esterification process is presented. This protocol provides a new and effective method to construct 4-alkylated 1,4-dihydropyridines with an ester fragment. Cyclic ether is employed as the C4 source of 1,4-dihydropyridines for the first time.

  提出了铁介导的烯胺酮、酸酐和四氢呋喃通过级联 [1 + 2 + 3]-环化/酯化过程的四组分反应。该方案提供了一种用酯片段构建 4-烷基化 1,4-二氢吡啶的新且有效的方法。首次采用环醚作为1,4-二氢吡啶的C4源。