N-(2,6-dimethylphenyl)methacrylamide | 54054-63-6

• 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: N-(2,6-dimethylphenyl)methacrylamide
• 英文别名: N-(2,6-dimethylphenyl)-2-methylprop-2-enamide
• CAS: 54054-63-6
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: WPXNHSRXGYBXNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-(2,6-dimethylphenyl)methacrylamide 在 indium(III) chloride 、 potassium tert-butylate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.0h， 生成
  参考文献：
  名称：

  Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening–Reclosure

  摘要：

  A novel and facile synthesis of azaspiro-gamma-lactones with a methylene-lactam framework from N-carbonyl imides is described. Mechanistic investigations provide evidence for a two-step reaction process involving ZnCl2-promoted addition of beta-amido allylindium species followed by an unexpectedly molecular-sieves-mediated ring opening-reclosure concomitantly with the loss of an N-carbonyl unit.

  DOI：

  10.1021/acs.orglett.5b03021
• 作为产物：
  描述：

  2,6-二甲基苯胺 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到N-(2,6-dimethylphenyl)methacrylamide
  参考文献：
  名称：

  从α，β-不饱和酰胺中多官能一锅法合成多取代的环戊2-亚胺类化合物：亚氨基-纳扎罗夫反应

  摘要：

  多取代的戊丹-1,4-二烯-3-亚胺的亚氨基-纳扎罗夫环化反应得以实现。为此，采用了一锅法，其中包括将α，β-不饱和仲酰胺与有机三氟硼酸钾进行还原性烯基亚氨基化，然后对多取代的戊丹-1,4-二烯-3-亚胺中间体进行酸催化的亚氨基-纳扎罗夫环化。有系统地研究。这种温和，操作简单，灵活且高产的方案有效地提供了多取代的戊丹-1,4-二烯-3-亚胺，环戊烯亚胺和α-氨基环戊烯酮，它们在有机合成中是有用的支架。通过密度泛函理论计算研究了多取代的戊丹-1,4-二烯-3-亚胺在C2位置的取代基效应。

  DOI：

  10.1002/anie.201805641

文献信息

• Iron-Mediated Azidomethylation or Azidotrideuteromethylation of Active Alkenes with Azidotrimethylsilane and Dimethyl Sulfoxide
  作者：Rui Zhang、Haifei Yu、Zejiang Li、Qinqin Yan、Pan Li、Jilai Wu、Jing Qi、Menglu Jiang、Lixian Sun

  DOI：10.1002/adsc.201800078

  日期：2018.4.3

  A radical azidomethylation of various alkenes with azidotrimethylsilane and dimethyl sulfoxide has been achieved under mild reaction conditions, and the method efficiently introduces common and valuable azide and methyl groups into organic compounds. It offers a convenient method for preparing organic azides, which can be easily transformed into related amine derivatives and N‐heterocycles. Control

  在温和的反应条件下，已实现了各种烯烃与叠氮基三甲基硅烷和二甲基亚砜的自由基叠氮甲基化，该方法有效地将常见且有价值的叠氮化物和甲基引入有机化合物。它提供了一种方便的方法来制备有机叠氮化物，可以轻松地将其转化为相关的胺衍生物和N杂环。提出了控制实验，例如捕获已开发系统的中间和克级反应以及反应产物的进一步转化。自由基参与反应过程。
• Antiarrythmic 1-arylcarbamoylalkyl-2-imidazoline derivatives,
  申请人：Berlex Laboratories, Inc.

  公开号：US04353921A1

  公开（公告）日：1982-10-12

  Novel 1,2-disubstituted imidazol(in)es are described herein. The compounds are generally produced by reacting a haloacylanilide with an excess of 2-substituted-imidazol(in)e. The compounds are antiarrhythmic agents.

  本文描述了一种1,2-二取代咪唑（酮）类化合物。通常通过将卤代酰苯胺与过量的2-取代咪唑（酮）反应来制备这些化合物。这些化合物是抗心律失常药物。
• Method of use of antiarrhythmic 1-arylcarbamoylalkyl imidazole
  申请人：Berlex Laboratories, Inc.

  公开号：US04415587A1

  公开（公告）日：1983-11-15

  Novel 1,2-disubstituted imidazol(in)es are described herein. The compounds are generally produced by reacting a haloacylanilide with an excess of 2-substituted-imidazol(in)e. The compounds are antiarrhythmic agents.

  本文描述了一种1,2-二取代咪唑（in）的小说化合物。这些化合物通常是通过将卤代酰苯胺与过量的2-取代咪唑（in）反应而产生的。这些化合物是抗心律失常药物。
• Solid State Photochemical Reaction of <i>N</i>-(α,β-Unsaturated carbonyl)benzoylformamides
  作者：Masami Sakamoto、Masaki Takahashi、Tsutomu Fujita、Shoji Watanabe、Takehiko Nishio、Ikuo Iida、Hiromu Aoyama

  DOI：10.1021/jo9704974

  日期：1997.9.1

  Photochemical reactions of various N-(alpha,beta-unsaturated carbonyl)benzoylfomamides both in solution and in a solid state were investigated. Under homogeneous conditions, all acyclic imides underwent photochemical 2 + 2 cycloaddition that resulted in the production of bicyclic oxetanes. N-Isopropyl- and N-benzyl-N-tigloylbenzoylformamides crystallized in a chiral space group, and the photolysis in the solid state yielded corresponding optic ally-active oxetanes. N-Tigloylbenzoylformanilide underwent cis-trans isomerization to yield a photostationary state (cis/trans = 1.3). Solid state oxetane formation of N-benzyl- and N-(o-tolyl)- and N-(2,6-xylpl)-N-tigloylbenzoylformamides progressed via the crystal-to-crystal pathway which was followed by X-ray powder diffraction, N-Benzyl-N-methacryloylbenzoylformamide crystallized in a chiral space group, and the solid state reaction led to an optically active beta-lactam via topochemically-controlled hydrogen abstraction by the alkenyl carbon atom. Photolysis of N-isopropyl-N-methacryloylbenzoylformamide in the solid state led to both oxetane formation and a transformation to azetidine-2,4-dione involving a 1,5-benzoyl shift.
• Sakamoto, Masami; Aoyama, Hiromu; Omote, Yoshimori, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1759 - 1762
  作者：Sakamoto, Masami、Aoyama, Hiromu、Omote, Yoshimori

  DOI：——

  日期：——