3,4-dimethoxy-N-methyl-N-phenylbenzamide | 1522-68-5

• 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: 3,4-dimethoxy-N-methyl-N-phenylbenzamide
• CAS: 1522-68-5
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: UBCNZNBUWMDAJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-N-methyl-N-phenylbenzamide 在 sodium persulfate 、 [(3-methoxy-N-methyl-N-phenylbenzamide)Pd(μ-TFA)]2 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以99%的产率得到5-methyl-8,9-dimethoxy-6(5H)-phenanthridone
  参考文献：
  名称：

  Cyclopalladation of N-phenylbenzamides: Synthesis and structure of bimetallic palladium(II)-complexes

  摘要：

  Three bimetallic palladium(II) complexes were generated by cyclopalladation of N-methyl-N-phenylbenzamide derivatives, substrates known to undergo oxidative intramolecular cross-coupling via palladium catalysis. These isolable Pd-complexes were characterized by X-ray crystallography. Stoichiometric and catalytic experiments with [(3-methoxy-N-methyl-N-phenylbenzamide)Pd(mu-TFA)](2) were investigated, and this palladium complex was found to be an effective precatalyst for oxidative cross-coupling. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.01.059
• 作为产物：
  描述：

  N,N-二甲基苯胺 、 藜芦酸 在 三乙烯二胺 、 四溴化碳 、 C₂₄H₂₁FeN₆O₂ 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以55%的产率得到3,4-dimethoxy-N-methyl-N-phenylbenzamide
  参考文献：
  名称：

  Redox noninnocence of the formazanate ligand applied to catalytic formation of α-ketoamides

  摘要：

  受欢迎的福马唑酸配体骨架的氧化还原非无辜性已被利用于电子转移和进一步合成α-酮酰胺，其由α-酮酸和胺组成。

  DOI：

  10.1039/d2cc02089k

文献信息

• Nickel-Catalyzed Claisen Condensation Reaction between Two Different Amides
  作者：Jiajia Chen、Man Xu、Subeen Yu、Yuanzhi Xia、Sunwoo Lee

  DOI：10.1021/acs.orglett.0c00485

  日期：2020.3.20

  A nickel-catalyzed Claisen condensation reaction between two amides, where one possesses an α-proton, for the synthesis of β-ketoamides was developed. Ni(glyme)Cl2 and terpyridine serve as the active catalysts in the presence of Mn and LiCl. N,N-Methylphenyl and N,N-diphenyl benzamide derivatives react with cyclic and noncyclic amides to give their corresponding β-ketoamides in moderate to good yields

  开发了一种镍催化的两种酰胺之间的克莱森缩合反应，其中一种酰胺具有α质子，可以合成β-酮酰胺。在Mn和LiCl存在下，Ni（glyme）Cl2和三联吡啶用作活性催化剂。N，N-甲基苯基和N，N-二苯基苯甲酰胺衍生物与环状和非环状酰胺反应，以中等至良好的产率得到它们相应的β-酮酰胺。另外，DFT计算表明还原消除是速率决定的步骤。
• OXIDISABLE PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE AS ANTI-ALZHEIMER AGENTS
  申请人：INSA (INSTITUT NATIONAL DES SCIENNCES APPLIQUÉES) DE ROUEN

  公开号：US20150353493A1

  公开（公告）日：2015-12-10

  A compound of formula (I) in which the dotted lines indicate the presence of at least one double bond; n=0 to 4; R 3 and R 4 are H, or when n=1, R 3 and R 4 can also form together a double bond between the carbon atoms, and m=0, 1 or 2, Z is CH or N or Z is C and —CHR 3 — is ═CH— linked by the double bond to cyclopentanone; or −(−) m - is absent, and Z is NH, >N-alkyl, >N-phenyl, >N-benzyl or >N heteroaryl; R 8 is alkyl, aryl or heteroaryl which can be optionally substituted; EWG represents an electron withdrawing group selected from the group comprising COOR, COSR, CONRR′, CN, COR, CF 3 , SOR, SO 2 R, SONRR′, SO 2 NRR′, NO 2 , halogen, heteroaryl; and the pharmaceutical salts and stereisomers thereof. The compounds of formula (I) are potent in the treatment of neurodegenerative diseases such as Alzheimer's disease.

  式(I)的化合物中，虚线表示存在至少一个双键；n = 0至4；R3和R4为H，或当n = 1时，R3和R4也可以共同形成碳原子之间的双键，m = 0、1或2，Z为CH或N，或者Z为C，-CHR3-与环戊酮通过双键连接，或-(-)m-不存在，Z为NH，>N-烷基，>N-苯基，>N-苯甲基或> N杂环芳基；R8为烷基、芳基或杂环芳基，可以选择性地被取代；EWG代表从COOR、COSR、CONRR'、CN、COR、CF3、SOR、SO2R、SONRR'、SO2NRR'、NO2、卤素、杂环芳基中选择的电子吸引基；以及其药物盐和立体异构体。式(I)的化合物在治疗神经退行性疾病，如阿尔茨海默病方面具有很强的疗效。
• A one-step base-free synthesis of <i>N</i>-arylamides <i>via</i> modified pivaloyl mixed anhydride mediated amide coupling
  作者：Fenghua Mao、Can Jin、Jie Wang、Hui Yang、Xinhuan Yan、Xiaoqing Li、Xiangsheng Xu

  DOI：10.1039/d3ob00452j

  日期：——

  Pivalic anhydride is shown to be an effective reagent for direct amidation of carboxylic acids with N-alkyl anilines. The only by-product of this reaction is nontoxic pivalic acid, which can be easily removed by aqueous workup. The reactions are conducted under mild conditions and found to be compatible with a range of carboxylic acids, including aromatic, heterocyclic, acrylic, and aliphatic carboxylic

  新戊酸酐被证明是一种有效的试剂，可用于羧酸与N-烷基苯胺的直接酰胺化。该反应的唯一副产物是无毒的新戊酸，可以通过水处理轻松去除。该反应在温和条件下进行，发现与一系列羧酸相容，包括芳香族、杂环、丙烯酸和脂肪族羧酸和氨基酸，可在短反应时间内生成所需的酰胺。
• US9376387B2
  申请人：——

  公开号：US9376387B2

  公开（公告）日：2016-06-28
• CN115557823
  申请人：——

  公开号：——

  公开（公告）日：——