4-乙酰基-N-苄基-N-甲基苯甲酰胺 | 1005460-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基-N-苄基-N-甲基苯甲酰胺
• 英文名称: 4-acetyl-N-benzyl-N-methylbenzamide
• CAS: 1005460-24-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: KVBLLXZUDMRHTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-乙酰基-N-苄基-N-甲基苯甲酰胺 在 (μ₃;η²;η³;η⁵-acenaphthylene)Ru3(CO)7 二甲基苯基硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以88%的产率得到p-(N-benzyl-N-methylaminomethyl)acetophenone
  参考文献：
  名称：

  分子催化剂的官能团选择性中毒：钌簇催化的高度酰胺选择性硅烷还原反应，不影响酮或酯。

  摘要：

  胺的添加消除了三钌簇在酮和酯的氢硅烷还原中的催化活性，而不会影响酰胺的还原速率。选择性还原了酰胺基酮和酰胺基酯中的酰胺基。

  DOI：

  10.1039/b711743d
• 作为产物：
  描述：

  N-甲基苄胺 在 N-氯代丁二酰亚胺 、 硫酸氧钒水合物 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 4-乙酰基-N-苄基-N-甲基苯甲酰胺
  参考文献：
  名称：

  Oxidovanadium(IV) sulfate catalyses light-driven C–N bond formation

  摘要：

  DOI：

  10.1016/j.mcat.2023.113054

文献信息

• Hydrosilane Reduction of Tertiary Carboxamides by Iron Carbonyl Catalysts
  作者：Yusuke Sunada、Hiroko Kawakami、Tsuyoshi Imaoka、Yukihiro Motoyama、Hideo Nagashima

  DOI：10.1002/anie.200905025

  日期：2009.12.7

  Fox in the carboxamide: Reduction of tertiary carboxamides to their corresponding amines is catalyzed by [Fe(CO)5] or [Fe3(CO)12], using 1,1,3,3‐tetramethyldisiloxane (TMDS) as the reducing agent. The reaction proceeds under either thermal or photochemical conditions. Unlike the hydrosilane reduction of amides using platinum or ruthenium catalysts, TMDS preferentially reduces a nitro group, even in

  羧酰胺中的Fox：[ 1,3,3,4-四甲基二硅氧烷（TMDS）]通过[Fe（CO）5 ]或[Fe 3（CO）12 ]催化叔羧酰胺还原为其相应的胺。反应在热或光化学条件下进行。与使用铂或钌催化剂对酰胺进行氢硅烷还原不同，TMDS即使在存在竞争性酰胺的情况下也优先还原硝基。
• Dioxygen-Promoted Pd-Catalyzed Aminocarbonylation of Organoboronic Acids with Amines and CO: A Direct Approach to Tertiary Amides
  作者：Long Ren、Xinwei Li、Ning Jiao

  DOI：10.1021/acs.orglett.6b02913

  日期：2016.11.18

  A direct approach from organoboronic acids and amines to tertiary amides via Pd-catalyzed aerobic aminocarbonylation has been developed. The presence of O2 significantly promotes the efficiency of this transformation. This method uses commercially available organoboronic acids and cheap CO and O2 (1 atm), which renders amides an easy synthesis with broad substrate scope and high functional group tolerance

  已经开发了通过Pd催化的需氧氨基羰基化反应从有机硼酸和胺到叔酰胺的直接方法。O 2的存在显着提高了这种转化的效率。该方法使用可商购的有机硼酸和廉价的CO和O 2（1 atm），这使得酰胺易于合成，具有广泛的底物范围和较高的官能团耐受性。
• Tandem Electro‐Thermo‐Catalysis for the Oxidative Aminocarbonylation of Arylboronic Acids to Amides from CO₂ and Water
  作者：Guoliang Mei、Yanze Lu、Xiaoju Yang、Sanxia Chen、Xuan Yang、Li‐Ming Yang、Conghui Tang、Yujie Sun、Bao Yu Xia、Bo You

  DOI：10.1002/anie.202314708

  日期：2024.1.8

  Direct CO₂ electroreduction to valuable chemicals is critical for carbon neutrality, while its main products are limited to simple C₁/C₂ compounds, and traditionally, the anodic O₂ byproduct is not utilized. We herein report a tandem electrothermo‐catalytic system that fully utilizes both cathodic (i.e., CO) and anodic (i.e., O₂) products during overall CO₂ electrolysis to produce valuable organic amides from arylboronic acids and amines in a separate chemical reactor, following the Pd(II)‐catalyzed oxidative aminocarbonylation mechanism. Hexamethylenetetramine (HMT)‐incorporated silver and nickel hydroxide carbonate electrocatalysts were prepared for efficient coproduction of CO and O₂ with Faradaic efficiencies of 99.3 % and 100 %, respectively. Systematic experiments, operando attenuated total reflection surface‐enhanced Fourier transform infrared spectroscopy characterizations and theoretical studies reveal that HMT promotes *CO₂ hydrogenation/*CO desorption for accelerated CO₂‐to‐CO conversion, and O₂ inhibits reductive deactivation of the Pd(II) catalyst for enhanced oxidative aminocarbonylation, collectively leading to efficient synthesis of 10 organic amides with high yields of above 81 %. This work demonstrates the effectiveness of a tandem electrothermo‐catalytic strategy for economically attractive CO₂ conversion and amide synthesis, representing a new avenue to explore the full potential of CO₂ utilization.

  摘要直接将二氧化碳电还原成有价值的化学品对实现碳中和至关重要，但其主要产物仅限于简单的 C1/C2 化合物，而且传统上并未利用阳极副产物 O2。我们在此报告了一种串联电醚催化系统，该系统在整个二氧化碳电解过程中充分利用阴极（即 CO）和阳极（即 O2）产物，在一个独立的化学反应器中，按照 Pd(II) 催化的氧化氨基羰基化机理，从芳基硼酸和胺中生产出有价值的有机酰胺。制备的六亚甲基四胺（HMT）掺杂碳酸氢银和掺杂碳酸氢镍电催化剂可高效共生 CO 和 O2，法拉第效率分别为 99.3 % 和 100 %。通过系统实验、操作性衰减全反射表面增强傅立叶变换红外光谱表征和理论研究发现，HMT 可促进*CO2 加氢/*CO 解吸以加速 到 CO 的转化，而 O2 可抑制 Pd(II) 催化剂的还原失活以增强氧化氨基羰基化，从而高效合成 10 种有机酰胺，产率高达 81% 以上。这项工作证明了串联电醚催化策略在具有经济吸引力的二氧化碳转化和酰胺合成方面的有效性，为充分挖掘二氧化碳的利用潜力开辟了一条新途径。
• Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si−H Groups Leads to High Efficiency and Selectivity
  作者：Shiori Hanada、Emi Tsutsumi、Yukihiro Motoyama、Hideo Nagashima

  DOI：10.1021/ja9055307

  日期：2009.10.21

  The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions The rate of the reaction is dependent on the distance of two Si-H groups, 1,1,3,3-tetramethyidisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, C=C, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.