4-bromo-N-cinnamylaniline | 22835-30-9

• 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: 4-bromo-N-cinnamylaniline
• 英文别名: 4-bromo-N-[(E)-3-phenylprop-2-enyl]aniline
• CAS: 22835-30-9
• 化学式: C₁₅H₁₄BrN
• 分子量: 288.187
• InChiKey: FIVMIDHISRIPQW-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  亚磷酸二丁酯 、 4-bromo-N-cinnamylaniline 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以68%的产率得到
  参考文献：
  名称：

  DDQ介导的仲胺与膦酸二烷基酯的交叉脱氢偶联反应

  摘要：

  这项工作报告了 DDQ 介导的仲胺与二烷基膦酸酯在温和条件下的交叉脱氢偶联反应。该反应在不涉及可见光或过渡金属催化的情况下高效进行。这种新方法提供了对生物学上重要的 α-氨基膦酸盐的有效访问。

  DOI：

  10.1055/s-0037-1611362
• 作为产物：
  描述：

  C6H5CHCHCHNC6H4Br-4 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以17.8 g的产率得到4-bromo-N-cinnamylaniline
  参考文献：
  名称：

  级联酰化/ IMDAV /烯反应序列的第一个例子，导致N-芳基苯并[ f ]异吲哚-4-羧酸具有抗病毒活性

  摘要：

  易于获得的N-芳基-3-苯基烯丙基胺与马来酸酐之间的反应产生了意想不到的产物-多取代的氢化苯并[ f ]异吲哚-4-羧酸。：这种转变通过的步骤的以前未知的序列前进Ñ与马来酸酐，在中间的乙烯基芳烃的分子内Diels-Alder反应的烯丙胺的酰化Ñ -maleamide，并且前两个步骤的产物的阿尔德烯反应。选定的苯并[ f ]异吲哚显示出抗病毒活性。

  DOI：

  10.1016/j.tetlet.2018.02.015

文献信息

• Solvent-Free Synthesis, DNA-Topoisomerase II Activity and Molecular Docking Study of New Asymmetrically N,N'-Substituted Ureas
  作者：Andressa Esteves-Souza、Claudio Rodrigues-Santos、Catarina Del Cistia、Daniel Silva、Carlos Sant'Anna、Aurea Echevarria

  DOI：10.3390/molecules171112882

  日期：——

  A new series of asymmetrically N,N'-substituted ureas 20–25 was prepared using solvent free conditions, which is an eco-friendly methodology, starting with Schiff bases derived from cinnamaldehyde and p-substituted anilines, which are subsequently submitted to reduction reactions that afford the corresponding asymmetric secondary amines. All of the intermediates were prepared using solvent free reactions, which were compared to traditional methodologies. All of the reactions required a remarkably short amount of time and provided good yields when solvent free conditions were employed compared to other methodologies. The DNA-topoisomerase II-α (topo II-α) activity was evaluated in relaxation assays, which showed that all of the compounds inhibited the enzyme activity at 10 μM, except for urea 24. Furthermore, a molecular docking study indicated that the compounds 20–25 binding to the topo II-α are able to interact with the same binding site as the anticancer drug etoposide, suggesting that the ureas could inhibit the enzyme by the same mechanism of action observed for etoposide, which prevents re-ligation of the DNA strands.

  采用无溶剂条件，以肉桂醛和p位取代的苯胺衍生的希夫碱为原料，经还原反应制得相应的非对称次级胺，进而合成了新系列非对称N,N'-取代的脲类化合物20–25。该方法是一种绿色环保的方法。所有中间体的制备均采用无溶剂反应，并与传统方法进行了比较。所有反应所需时间都极短，且在采用无溶剂条件时的产率普遍高于其他方法。通过松弛实验评估了这些化合物对DNA拓扑异构酶II-α（topo II-α）的活性。结果表明，除脲24外，所有化合物在10 μM浓度下均抑制酶活性。此外，分子对接研究显示，化合物20–25与topo II-α的结合位点与抗癌药物依托泊苷相同，这表明脲类化合物可能通过类似依托泊苷的机制抑制酶活性，即阻止DNA链的再连接。
• Indium-Mediated Addition of γ-Substituted Allylic Halides to N-Aryl α-Imino Esters: Diastereoselective Production of β,β′-Disubstituted α-Amino Acid Derivatives with Two Contiguous Stereocenters
  作者：Nayyar Ahmad Aslam、Vadla Rajkumar、Chennakesava Reddy、Makoto Yasuda、Akio Baba、Srinivasarao Arulananda Babu

  DOI：10.1002/ejoc.201200254

  日期：2012.8

  γ-substituted allylic halides to N-aryl (including N-PMP) α-imino- and N-acylhydrazono esters and highly diastereoselective tailoring of functionalized γ,δ-unsaturated β,β′-disubstituted N-aryl α-amino acid derivatives, bearing two contiguous stereocenters is reported. Further N-allylation of the resulting γ,δ-unsaturated β,β′-disubstituted N-aryl amino acid derivatives followed by ring closing metathesis (RCM)

  螯合控制的 Barbier 型铟介导的 γ-取代的烯丙基卤化物与 N-芳基（包括 N-PMP）α-亚氨基和 N-酰基腙酯的加成以及功能化 γ,δ-不饱和 β,β' 的高度非对映选择性定制-二取代的 N-芳基 α-氨基酸衍生物，带有两个连续的立体中心。所得 γ,δ-不饱和 β,β'-二取代 N-芳基氨基酸衍生物的进一步 N-烯丙基化，然后进行闭环复分解 (RCM)，合成了带有两个连续立体中心的 2,3-二取代 N-芳基四氢吡啶衍生物. 关键产品的立体化学是通过 X 射线结构分析明确确定的。
• Chiral Brønsted Acid Catalyzed Enantioselective Phosphonylation of Allylamine via Oxidative Dehydrogenation Coupling
  作者：Ming-Xing Cheng、Ran-Song Ma、Qiang Yang、Shang-Dong Yang

  DOI：10.1021/acs.orglett.6b01514

  日期：2016.7.1

  A new strategy for the synthesis of chiral α-amino phosphonates by enantioselective C–H phosphonylation of allylamine with phosphite in the presence of a chiral Brønsted acid catalyst has been developed. This protocol successfully integrates direct C–H oxidation with asymmetric phosphonylation and exhibits high enantioselectivity.

  在手性布朗斯台德酸催化剂的存在下，开发了一种通过烯丙基胺与亚磷酸酯的对映体C–H膦酰基对映体选择性合成手性α-氨基膦酸酯的新策略。该方案成功地将直接的C–H氧化与不对称的膦酰化反应相结合，并显示出高对映选择性。
• First example of the cascade acylation/IMDAV/ene reaction sequence, leading to N-arylbenzo[f]isoindole-4-carboxylic acids possessing anti-viral activity
  作者：Alexander A. Voronov、Kseniia A. Alekseeva、Elena A. Ryzhkova、Vladimir V. Zarubaev、Anastasia V. Galochkina、Vladimir P. Zaytsev、Mahesh S. Majik、Santosh G. Tilve、Atash V. Gurbanov、Fedor I. Zubkov

  DOI：10.1016/j.tetlet.2018.02.015

  日期：2018.3

  The reaction between readily accessible N-aryl-3-phenylallylamines and maleic anhydride led to unexpected products – polysubstituted hydrogenated benzo[f]isoindole-4-carboxylic acids. This transformation proceeds through a previously unknown sequence of steps: N-acylation of the allylamine with maleic anhydride, intramolecular Diels-Alder reaction of the vinylarene in the intermediate N-maleamide,

  易于获得的N-芳基-3-苯基烯丙基胺与马来酸酐之间的反应产生了意想不到的产物-多取代的氢化苯并[ f ]异吲哚-4-羧酸。：这种转变通过的步骤的以前未知的序列前进Ñ与马来酸酐，在中间的乙烯基芳烃的分子内Diels-Alder反应的烯丙胺的酰化Ñ -maleamide，并且前两个步骤的产物的阿尔德烯反应。选定的苯并[ f ]异吲哚显示出抗病毒活性。
• DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates
  作者：Ming-Xing Cheng、Jing-Wei Lei、Cai-Xia Xie

  DOI：10.1055/s-0037-1611362

  日期：2019.1

  This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approach provides efficient access to biologically important α-aminophosphonates.

  这项工作报告了 DDQ 介导的仲胺与二烷基膦酸酯在温和条件下的交叉脱氢偶联反应。该反应在不涉及可见光或过渡金属催化的情况下高效进行。这种新方法提供了对生物学上重要的 α-氨基膦酸盐的有效访问。