methyl 4-methylbenzimidate | 56108-06-6

• 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: methyl 4-methylbenzimidate
• 英文别名: methyl 4-methylbenzenecarboximidate
• CAS: 56108-06-6
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: IMIWDCNFWJFIKT-UHFFFAOYSA-N

物化性质

• 沸点：
  191.7±33.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-methylbenzimidate 在 甲醇 、 sodium 作用下， 反应 39.0h， 生成 2,4-Dioxo-3-phenyl-6-p-tolyl-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Pyrimidine-5-carbonitriles from MethylN-(Aminocarbonyl)- orN-(Aminothiocarbonyl)-imidates

  摘要：

  通过 N-（氨基羰基）- 或 N-（氨基硫代羰基）亚胺酸甲酯与丙二腈、氰乙酸甲酯或丙二酸二乙酯的反应，可以制备一些取代的嘧啶-5-甲腈和嘧啶-5-甲酸乙酯。

  DOI：

  10.1055/s-1988-27485
• 作为产物：
  描述：

  甲醇 、 对甲苯腈 在 乙酰氯 作用下， 反应 24.0h， 生成 methyl 4-methylbenzimidate
  参考文献：
  名称：

  Flow Rhodaelectro-Catalyzed Alkyne Annulations by Versatile C–H Activation: Mechanistic Support for Rhodium(III/IV)

  摘要：

  A flow-metallaelectro-catalyzed C-H activation was realized in terms of robust rhodaelectro-catalyzed alkyne annulations. To this end, a modular electro-flow cell with a porous graphite felt anode was designed to ensure efficient turnover. Thereby, a variety of C-H/N-H functionalizations proved amenable for alkyne annulations with high levels of regioselectivity and functional group tolerance, viable in both an inter- or intramolecular manner. The electro-flow C-H activation allowed easy scale up, while in-operando kinetic analysis was accomplished by online flow-NMR spectroscopy. Mechanistic studies suggest an oxidatively induced reductive elimination pathway on rhodium(III) in an electrocatalytic regime.

  DOI：

  10.1021/jacs.9b07763

文献信息

• Electrochemical Access to Aza‐Polycyclic Aromatic Hydrocarbons: Rhoda‐Electrocatalyzed Domino Alkyne Annulations
  作者：Wei‐Jun Kong、Zhigao Shen、Lars H. Finger、Lutz Ackermann

  DOI：10.1002/anie.201914775

  日期：2020.3.27

  Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza-PAHs was developed via a rhodium-catalyzed cascade C-H activation and alkyne annulation. A multifunctional O-methylamidoxime enabled the high chemo- and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible

  氮掺杂多环芳烃（氮杂-PAHs）已在材料科学中得到广泛应用。本文中，通过铑催化的级联CH活化和炔烃环化反应开发了氮杂-PAHs的模块化电化学合成方法。多功能的O-甲基ami胺肟具有很高的化学和区域选择性。两个关键的rhodocyclic中间体的分离使得有可能描绘出三个CH活化步骤的确切顺序。此外，金属电催化的多CH转化具有独特的官能团耐受性，包括高反应性的碘基和叠氮基。
• Quinazoline Synthesis via Rh(III)-Catalyzed Intermolecular C–H Functionalization of Benzimidates with Dioxazolones
  作者：Jie Wang、Shanke Zha、Kehao Chen、Feifei Zhang、Chao Song、Jin Zhu

  DOI：10.1021/acs.orglett.6b00691

  日期：2016.5.6

  An efficient double C–N bond formation sequence to prepare highly substituted quinazolines utilizing benzimidates and dioxazolones under the catalytic redox-neutral [Cp*RhCl2]2/AgBF4 system, where dioxazolones could work as an internal oxidant to maintain the catalytic cycle, is reported. N-Unsubstituted imine not only acts as a directing group but also functions as a nucleophile in postcoupling cyclization

  在催化氧化还原中性[Cp * RhCl 2 ] 2 / AgBF 4体系下，利用苯甲二酸盐和二恶唑酮制备高效取代的C–N键形成顺序的方法，其中二恶唑酮可作为内部氧化剂来维持催化循环，被报道。N-未取代的亚胺在后偶联环化中不仅充当引导基团，而且还充当亲核试剂，并且二恶唑酮充当访问杂环的偶联伴侣。
• An Inverse Electron Demand Azo-Diels–Alder Reaction of <i>o</i>-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines
  作者：Dmitry V. Osipov、Vitaly A. Osyanin、Guzel’ D. Khaysanova、Elvira R. Masterova、Pavel E. Krasnikov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.8b00692

  日期：2018.4.20

  the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels–Alder reaction, and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.

  我们已经研究了邻醌甲基化物前体与亚氨基醚的反应。该反应提供了取代的1，3-苯并恶嗪的通用途径。拟议的反应机制涉及邻醌甲基化物中间体的产生，亚氨基-狄尔斯-阿尔德反应和消除。这种级联过程是亚氨基醚作为亲双烯体参与的罕见例子。
• Synthesis of isoquinolines via Rh-catalyzed C–H activation/C–N cyclization with diazodiesters or diazoketoesters as a C₂ source
  作者：Jie Wang、Shanke Zha、Kehao Chen、Feifei Zhang、Jin Zhu

  DOI：10.1039/c6ob00901h

  日期：——

  Synthesis of isoquinolines based on efficient C–C and C–N bond formation through Rh(III)-catalyzed C–H activation and subsequent intramolecular cyclization is reported. Diazodiesters serving as a C2 source in the newly formed heterocycles are first demonstrated. Additionally, the Rh(III)-catalyzed direct C–H activation/cyclization of benzimidates with diazoketoesters is also described.

  据报道，通过Rh（III）催化的C–H活化和随后的分子内环化作用，基于有效的C–C和C–N键的形成，合成了异喹啉。首先证明了在新形成的杂环中用作C 2源的重氮二酯。此外，还描述了Rh（III）催化的重氮苄酯与重氮酮酸酯的直接CH活化/环化。
• FXA INHIBITORS WITH CYCLIC AMIDINES AS P4 SUBUNIT, PROCESSES FOR THEIR PREPARATIONS, AND PHARMACEUTICAL COMPOSITIONS AND DERIVATIVES THEREOF
  申请人：Cho Young Lag

  公开号：US20100184781A1

  公开（公告）日：2010-07-22

  The present invention relates to novel oxazolidinone derivatives with cyclic amidines, and prodrugs, hydrates, solvates, isomers and pharmaceutically acceptable salts thereof, and processes for preparing the same, and pharmaceutical compositions comprising the same. The oxazolidinone derivatives with cyclic amidines, and prodrugs, hydrates, solvates, isomers and pharmaceutically acceptable salts thereof can be usefully employed as an anticoagulant for treating thromboembolism and tumors via inhibition of coagulation factor Xa.

  本发明涉及具有环状酰胺的新型噁唑啉酮衍生物及其前药、水合物、溶剂合物、异构体和药学上可接受的盐，以及制备它们的过程和包含它们的药物组合物。具有环状酰胺的噁唑啉酮衍生物及其前药、水合物、溶剂合物、异构体和药学上可接受的盐可用作抗凝剂，通过抑制凝血因子Xa治疗血栓栓塞和肿瘤。