N-(4-bromobenzyl)-3-phenylpropiolamide | 1284971-52-3

• 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: N-(4-bromobenzyl)-3-phenylpropiolamide
• 英文别名: N-[(4-bromophenyl)methyl]-3-phenylprop-2-ynamide
• CAS: 1284971-52-3
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: QPFUIAPZHZTBDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-戊烯-1-醇 、 N-(4-bromobenzyl)-3-phenylpropiolamide 在 copper chloride dihydrate 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以88%的产率得到(Z)-N-(4-bromobenzyl)-3-chloro-3-phenyl-2-((tetrahydrofuran-2-yl)methyl)acrylamide
  参考文献：
  名称：

  Nucleopalladation-Initiated Oxyalkenylation of Alkenes: A Strategy To Construct Functionalized Oxygenated Heterocycles

  摘要：

  A convenient and efficient approach to construct functionalized oxygen heterocycles, i.e., tetrahydrofurans, tetrahydropyrans, and γ-lactones, has been reported. This process successfully provides a route to construct derivatives of naturally occurring biologically active tetrahydrofurans, especially ones with spirocyclic structure. Highly regio- and stereoselective nucleopalladation of alkynes initiates the cross-coupling between alkynamides and alkenes to give the olefin oxyalkenylation products in good to excellent yields. The hydroxyl group in the olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination.

  DOI：

  10.1021/jo501317v
• 作为产物：
  描述：

  碘苯 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 N-(4-bromobenzyl)-3-phenylpropiolamide
  参考文献：
  名称：

  电催化三组分反应：抗癌剂含碲恶唑烷酮的合成

  摘要：

  有机碲化合物的合成在药物科学中至关重要。在此，我们开发了一种新型高效的电化学催化炔丙酰胺或炔丙胺与CO 2 和二碲的多组分反应，并据我们所知首次在温和条件下合成了多种含碲2-恶唑烷酮，且收率令人满意。状况。此外，通过使用针对各种类型的人类癌细胞的MTT测定法，测试了所得的含碲2-恶唑烷酮的体外抗癌活性。化合物5e与其他恶唑烷酮和含硒恶唑烷酮化合物相比，显示出更好的抗肿瘤活性。这些发现为有机碲化合物的合成提供了新的策略，也为含硫有机化合物的生物活性研究提供了新的视角。

  DOI：

  10.1039/d3gc01288c

文献信息

• A Gold‐Catalyzed Acid‐Assisted Regioselective Cyclization for the Synthesis of Polysubstituted Oxazoles
  作者：Qian Wang、Stephanie Hoffmann、Jasmin Schießl、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/ejoc.201900699

  日期：2020.5.3

  derivatives are obtained through a regioselective gold‐catalyzed reaction of α‐alkynylamides and alkynoates in the presence of nitriles. The intermediary obtained gold carbenes are generated by an alkyne oxidation with a pyridine N‐oxide. Acidic conditions ensure that only one of the two carbonyl oxygen atoms in these intermediates selectively cyclizes to the products in excellent yields.

  多取代的恶唑衍生物是通过在腈存在下，α-炔基酰胺和炔酸的区域选择性金催化反应获得的。中间体获得的金卡宾是通过吡啶N-氧化物进行炔烃氧化而生成的。酸性条件确保这些中间体中的两个羰基氧原子中只有一个以优良的收率选择性地环化成产物。
• Palladium/Copper Bimetallic System-Mediated Cross-Coupling of Alkynes and Alkenes: Two Strategies to Suppress β-H Elimination on Alkyl-Palladium Center
  作者：Liangbin Huang、Qian Wang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1002/adsc.201400007

  日期：2014.6.16

  efficient strategies to suppress β‐H elimination during the palladium/copper bimetallic system‐mediated cross‐coupling between alkynamides and alkenes. Remote donor groups with the terminal olefins, such as toluenesulfonamide, phosphate, sulfone, etc., cooperate with the amide of alkynamides and chelate the palladium active center, to promote C(sp3)O bond formation by suppressing the β‐H elimination

  本文介绍了两种有效的策略来抑制炔/酰胺与烯烃之间的钯/铜双金属系统介导的交叉偶联过程中的β-H消除。带有末端烯烃的远端供体基团，例如甲苯磺酰胺，磷酸酯，砜等，与炔基酰胺的酰胺配合并螯合钯活性中心，通过抑制β-H的消除促进C（sp 3）O键的形成。另一个策略使用的降冰片烯的刚性结构，使中间没有顺-β-氢实现的C的还原消除 Cl键。
• Electrocatalytic three-component reactions: synthesis of tellurium-containing oxazolidinone for anticancer agents
  作者：Xue-Qi Zhou、Hai-Tao Tang、Fei-Hu Cui、Ying Liang、Shu-Hui Li、Ying-Ming Pan

  DOI：10.1039/d3gc01288c

  日期：——

  assay against various types of human cancer cells. Compound 5e showed better antitumor activity than did the other oxazolidinone and selenium-containing oxazolidinone compounds. These findings have provided new synthetic strategies for organotellurium compounds and have shown a new perspective for the study of the biological activity of chalcogen-containing organic compounds.

  有机碲化合物的合成在药物科学中至关重要。在此，我们开发了一种新型高效的电化学催化炔丙酰胺或炔丙胺与CO 2 和二碲的多组分反应，并据我们所知首次在温和条件下合成了多种含碲2-恶唑烷酮，且收率令人满意。状况。此外，通过使用针对各种类型的人类癌细胞的MTT测定法，测试了所得的含碲2-恶唑烷酮的体外抗癌活性。化合物5e与其他恶唑烷酮和含硒恶唑烷酮化合物相比，显示出更好的抗肿瘤活性。这些发现为有机碲化合物的合成提供了新的策略，也为含硫有机化合物的生物活性研究提供了新的视角。
• Nucleopalladation-Initiated Oxyalkenylation of Alkenes: A Strategy To Construct Functionalized Oxygenated Heterocycles
  作者：Liangbin Huang、Qian Wang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo501317v

  日期：2014.8.15

  A convenient and efficient approach to construct functionalized oxygen heterocycles, i.e., tetrahydrofurans, tetrahydropyrans, and γ-lactones, has been reported. This process successfully provides a route to construct derivatives of naturally occurring biologically active tetrahydrofurans, especially ones with spirocyclic structure. Highly regio- and stereoselective nucleopalladation of alkynes initiates the cross-coupling between alkynamides and alkenes to give the olefin oxyalkenylation products in good to excellent yields. The hydroxyl group in the olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination.
• Electrochemically Mediated Fixation of CO₂: Synthesis of Functionalized Oxazolidine‐2,4‐Diones by Three‐Component Reactions
  作者：Ting‐Kai Xiong、Qiang Xia、Xue‐Qi Zhou、Shu‐Hui Li、Fei‐Hu Cui、Hai‐Tao Tang、Ying‐Ming Pan、Ying Liang

  DOI：10.1002/adsc.202300396

  日期：2023.7.4

  Carbon dioxide is a harmful greenhouse gas, as well as a valuable resource. Here, a three-component cyclization reaction was developed for the synthesis of oxazolidine-2,4-diones by immobilizing CO2 under the electrochemistry and copper catalyst. Propargyl amide was used as the reaction substrate to capture carbon dioxide to produce carboxyl anion, while selenide produced electrophilic receptor to

  二氧化碳是一种有害的温室气体，也是一种宝贵的资源。在此，开发了一种三组分环化反应，通过在电化学和铜催化剂下固定CO 2来合成恶唑烷-2,4-二酮。以丙炔酰胺为反应底物捕获二氧化碳产生羧基阴离子，而硒化物在电化学条件下产生亲电受体激活三键。然后进行分子内环化反应，得到目标产物。通过这种环境友好的策略，合成了一系列重要的恶唑烷-2,4-二酮。