3-(4-methylphenyl)propenoic acid N-methylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-methylphenyl)propenoic acid N-methylamide
• 英文别名: N-methyl-3-(4-methylphenyl)prop-2-enamide
• 化学式: C₁₁H₁₃NO
• mdl: MFCD19595588
• 分子量: 175.23
• InChiKey: IHKAXKHYYPDPML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  3-(4-methylphenyl)propenoic acid N-methylamide 在 碘苯二乙酸 、 硫酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以57%的产率得到N-methyl-2-oxo-2-phenylacetamide
  参考文献：
  名称：

  无金属的串联氧化芳基迁移和C–C键裂解：由丙烯酸衍生物合成α-酮酰胺和酯

  摘要：

  已经发现了一种由高价碘试剂介导的新型无金属串联氧化芳基迁移/ CC键断裂反应。所提出的转变通过伴随CC键断裂的1，2-芳基转移的协同过程，使人们容易地从丙烯酸衍生物中直接获得重要的α-酮酰胺和α-酮酸酯衍生物。

  DOI：

  10.1021/ol502834g
• 作为产物：
  描述：

  对甲基肉桂酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 3-(4-methylphenyl)propenoic acid N-methylamide
  参考文献：
  名称：

  Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

  摘要：

  Cinnamides ArCH=CHCONRR' in reactions with arenes Ar'H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give C=C bond hydroarylation products ArAr'CHCH2CONRR' in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr'CHCH2CH2NRR', valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR', have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.033

文献信息

• Dual Role of the Rhodium(III) Catalyst in C–H Activation: [4 + 3] Annulation of Amide with Allylic Alcohols to 7-Membered Lactams
  作者：Mahadev Sharanappa Sherikar、Ravi Devarajappa、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.1c00048

  日期：2021.3.19

  Rh-catalyst, forming the corresponding alkylated products. Mechanistic studies show that AgSbF6 is also playing a dual role. Apart from being a halide scavenger, AgSbF6 catalyzes the cyclization of the alkylated product, forming the desired lactam. The current method has good synthetic application and is useful for synthesizing a few biologically active compounds that can act as the dopamine D3 receptor

  [4 + 3]据报道，Rh（III）催化使用烯丙醇作为偶合伴侣，对伯，仲苯甲酰胺和肉桂酰胺衍生物进行环化，其中Rh（III）扮演氧化剂和C–H催化剂的双重角色激活。Rh催化剂将烯丙醇氧化成其羰基衍生物，并且在Rh催化剂的存在下原位生成的羰基化合物与苯甲酰胺反应，形成相应的烷基化产物。机理研究表明，AgSbF 6也起着双重作用。除了是卤化物的清除剂，AgSbF 6催化烷基化产物的环化反应，形成所需的内酰胺​​。目前的方法具有良好的合成应用，可用于合成一些可以用作多巴胺D 3受体配体的生物活性化合物，包括小ber碱样类似物。氘代研究和控制实验帮助我们提出了机理。
• Liquid composition for bulging mucous membrane for use in endoscopic surgery comprising a chitosan derivative containing carbohydrate chains
  申请人：Hayashi Takuya

  公开号：US20070078108A1

  公开（公告）日：2007-04-05

  The present invention provides a liquid composition to make the mucous membrane bulge during endoscopic surgery characterized in that it comprises a chitosan derivative containing carbohydrate chains. The use of the composition of the present invention as a liquid for bulging the mucous membrane during endoscopic surgery, maintain the bulge of the mucous membrane for a long period, and prevent perforation, resulting in the improved reliability of endoscopic surgery. The composition of the present invention also demonstrates prevention and inhibition of bleeding from the incised portion. The introduction of a photo-reactive group to the above chitosan derivative with carbohydrate chains allows the easy formation of a hydrogel through photo-crosslinking, leading to the further improvement in retention of the bulge and prevention of bleeding.
• MEDICAL COMPOSITION FOR PROMOTION OF SKIN REGENERATION
  申请人：Kanatani Yasuhiro

  公开号：US20100056462A1

  公开（公告）日：2010-03-04

  The present invention provides a medical composition which, in autotransplantation which is the only method that can induce the epithelialization even in a widespread full-thickness skin defect, enables the fixation of an autotransplantation skin graft in a simple manner and can increase the efficiency of epithelialization to promote the regeneration of the skin. The present invention elates to a medical composition comprising a photo-crosslinkable chitosan derivative and an amino acid and/or a saccharide. The amino acid is preferably an essential amino acid, and the saccharide is preferably a neutral saccharide selected from glucose, galactose, mannose and fucose.
• ANTI-TUMOR COMPOSITION COMPRISING TISSUE-ACCUMULATING CHITOSAN GEL
  申请人：Ishihara Masayuki

  公开号：US20100093660A1

  公开（公告）日：2010-04-15

  The present invention is achieved based on a novel finding that chitosan gel having retentivity in tissue has an antitumor activity and provides an antitumor composition containing chitosan gel having retentivity in tissue. The chitosan gel having retentivity in tissue of the present invention is preferably chitosan gel formed of a chitosan derivative having a carbohydrate chain introduced thereto as a base, to which a photoreactive group is further introduced to form crosslink with photo-irradiation; or chitosan gel formed of a polyion complex, which is formed of a carbohydrate chain-containing chitosan derivative and another substance, for example, an acidic polysaccharide. The antitumor composition of the present invention can suppress growth of a tumor without bringing it into contact with the tumor but by simply arranging it near the tumor.
• US7476659B2
  申请人：——

  公开号：US7476659B2

  公开（公告）日：2009-01-13