N-(2-乙基苯基)苯甲酰胺 | 78987-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-乙基苯基)苯甲酰胺
• 英文名称: 2'-Ethylbenzanilide
• 英文别名: N-(2-ethylphenyl)benzamide；benzoic acid-(2-ethyl-anilide)；Benzoesaeure-(2-aethyl-anilid)；2-Benzamino-1-aethyl-benzol；2-Aethyl-N-benzoyl-anilin；Benzo-2-aethyl-anilid
• CAS: 78987-16-3
• 化学式: C₁₅H₁₅NO
• mdl: MFCD00791169
• 分子量: 225.29
• InChiKey: NSDKDLAEYFSRJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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-乙基苯基)苯甲酰胺 在 copper(II) bis(trifluoromethanesulfonate) 、 双三氟甲烷磺酰亚胺 、 Selectfluor 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以84%的产率得到4-methyl-2-phenyl-4H-benzo[d][1,3]oxazine
  参考文献：
  名称：

  的铜催化选择性苄型C-O环化ñ - ø -Tolylbenzamides：4的合成ħ -3,1-苯并恶嗪

  摘要：

  报道了一种新颖的Selectfluor介导的铜催化的高选择性苄基C–O环化反应，用于合成4 H -3,1-苯并恶嗪。在N - o-甲苯基苯甲酰胺中，相对于芳族C（sp 2）-H键，苄基C（sp 3）-H具有主要的选择性。

  DOI：

  10.1021/ol301492d
• 作为产物：
  描述：

  2-乙基苯胺 在 Oxone 、 辛酸铑 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 N-(2-乙基苯基)苯甲酰胺
  参考文献：
  名称：

  Synthesis of N-Acylamidines via Rhodium-Catalyzed Reaction of Nitrosobenzene Derivatives with N-Sulfonyl-1,2,3-triazoles

  摘要：

  alpha-Imino rhodium carbene, readily generated from N-sulfonyl-1,2,3-triazole, underwent cycloaddition and subsequent rearrangement with a nitrosobenzene derivative to afford N-acylamidine. The unprecedented CC bond cleavage of a-imino carbene was facilitated by the weakness of the NO bond.

  DOI：

  10.1021/ol5031876

文献信息

• Efficient and Selective Hydrosilylation of Secondary and Tertiary Amides Catalyzed by an Iridium(III) Metallacycle: Development and Mechanistic Investigation
  作者：Yann Corre、Xavier Trivelli、Frédéric Capet、Jean-Pierre Djukic、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1002/cctc.201700400

  日期：2017.6.8

  Readily accessible cationic IrIII metallacycles catalyze efficiently the chemoselective hydrosilylation of tertiary and secondary amides to amines. The catalyst described herein operates at low loadings using inexpensive 1,1,3,3-tetramethyldisiloxane and allows fast reactions with high yields, selectivities, and turnover numbers. A transient iminium intermediate has been observed for the first time

  易于获得的阳离子Ir III金属环有效催化叔酰胺和仲酰胺向胺的化学选择性氢化硅烷化。本文所述的催化剂使用廉价的1,1,3,3-四甲基二硅氧烷在低负荷下操作，并允许以高产率，选择性和周转数进行快速反应。通过质谱法首次观察到了过渡亚胺鎓中间体，并通过DFT计算研究了催化剂和硅烷试剂的活化。这些基本见解通过适当的配体修饰来支持Ir III金属环的当前和未来的改进，并使基于金属环的催化剂能够进一步广泛应用。
• [EN] 5-LIPOXYGENASE INHIBITORS<br/>[FR] INHIBITEURS DE 5-LIPOXYGÉNASE
  申请人：RANBAXY LAB LTD

  公开号：WO2012014127A1

  公开（公告）日：2012-02-02

  The present invention relates to sulfonamides derivatives as 5-lipoxygenase (5-LO) inhibitors and a process for their synthesis. The present invention also relates to pharmacological compositions containing these sulfonamides derivatives, as well as methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, Type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders.

  本发明涉及磺胺类衍生物作为5-脂氧合酶（5-LO）抑制剂以及它们的合成方法。本发明还涉及含有这些磺胺类衍生物的药物组合物，以及治疗支气管哮喘、慢性阻塞性肺疾病、类风湿关节炎、多发性硬化症、I型糖尿病、牛皮癣、移植物排斥反应、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒症、过敏性鼻炎和其他炎症和/或自身免疫性疾病的方法。
• Activation of the Aryl Hydrocarbon Receptor by Methyl Yellow and Related Congeners: Structure-Activity Relationships in Halogenated Derivatives.
  作者：Taka-aki Kato、Tomonari Matsuda、Saburo Matsui、Takaharu Mizutani、Ken-ichi Saeki

  DOI：10.1248/bpb.25.466

  日期：——

  The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure–activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2′- and 6′-position), and reduction by substitution at the para-position (4′-position). The greatest enhancement of the ligand activity was observed in 2′,6′-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4′-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2′)-chlorine-substitution, and the AhR ligand activity of 2′,4′-dichlorobenzanilide was similar to that of 2′-chloro-MY. These results suggest that the amide bond is equivalent to the –N=N– or –CH=CH– double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.

  芳香烃受体(AhR)是一种配体激活的转录因子，可介导多种环境化合物的生物作用。甲基黄(4-二甲氨基偶氮苯；MY)是一种主要的偶氮染料，通过使用酵母AhR信号检测方法，对结构相关化合物进行了结构-活性关系分析，以评估其作为AhR配体的特性。 对23种卤代甲基黄的AhR配体活性的卤素取代效应可总结如下：邻位(2'和6'位)的卤素取代增强活性，对位(4'位)取代则降低活性。2',6'-二氯代甲基黄表现出最强的配体活性增强效果(是MY的13.5倍)，其AhR配体活性与2,3,7,8-四氯二苯并-p-二恶英(TCDD)在本检测系统中的活性非常接近。 在研究与MY结构相关的化合物时发现，苯甲酰苯胺(BA)显示出与偶氮苯和反式二苯乙烯几乎相同的AhR配体活性。此外，分子长度与MY相似的4'-氯代苯甲酰苯胺通过邻位(2')氯取代增强了AhR配体活性，2',4'-二氯代苯甲酰苯胺的AhR配体活性与2'-氯代-MY相似。 这些结果表明，在1,2-二苯基-1,2-烯衍生物中，酰胺键与-N=N-或-CH=CH-双键在被AhR识别为配体时具有等效作用。
• Potassium <i>tert</i> -Butoxide Prompted Highly Efficient Transamidation and Its Coordination Radical Mechanism
  作者：Zhiyong Tan、Zhenhua Li、Yao Ma、Jinjing Qin、Chuanming Yu

  DOI：10.1002/ejoc.201900666

  日期：2019.7.31

  A simple and highly efficient protocol was developed for the transamidation of N,N‐disubstituted amides with primary amines in the presence of potassium tert‐butoxide, affording desired products in good to excellent yields. Experimental investigation revealed that an unprecedented coordination radical process enhanced this transformation.

  开发了一种简单高效的方案，用于在叔丁醇钾存在下将N，N-二取代酰胺与伯胺进行氨基转移，从而以良好的收率提供了所需的产物。实验研究表明，前所未有的协调性激进过程增强了这种转变。
• Buchwald–Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd–NHC complex
  作者：Di-Zhong Zheng、Hong-Gang Xiong、A-Xiang Song、Hua-Gang Yao、Chang Xu

  DOI：10.1039/d1ob02051j

  日期：——

  A modular and generic method for the Buchwald–Hartwig amination reactions of relatively unreactive aryl esters as acyl electrophiles and aryl chlorides as aryl electrophiles has been developed, leading to the efficient synthesis of amides/amines under air conditions and with low catalyst loadings. The success of this catalytic protocol is mainly attributed to the modification of the Pd–IPr skeleton

  已经开发了一种模块化和通用的方法，用于将相对不活泼的芳基酯作为酰基亲电试剂和芳基氯化物作为芳基亲电试剂进行 Buchwald-Hartwig 胺化反应，从而在空气条件下和低催化剂负载下有效合成酰胺/胺。该催化方案的成功主要归功于 Pd-IPr 骨架的空间位阻和供电子苯甲醚基团的修饰。该方法还具有良好的官能团耐受性和优异的化学选择性。总之，本文提出的结果表明，有可能为不同的亲电试剂开发一种通用的通用方案以进行 Buchwald-Hartwig 胺化反应，避免过多考虑底物依赖性 C-N 键形成的反应条件。

表征谱图