N-(3,5-二甲基苯基)-3-硝基苯甲酰胺 | 102631-08-3

• 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-(3,5-二甲基苯基)-3-硝基苯甲酰胺
• 英文名称: N-(3,5-dimethylphenyl)-3-nitrobenzamide
• CAS: 102631-08-3
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD00783867
• 分子量: 270.288
• InChiKey: OIZWLGYRGCTUFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,5-二甲基苯基)-3-硝基苯甲酰胺 在 palladium on activated charcoal 氢气 作用下， 反应 3.0h， 以50%的产率得到3-氨基-n-(3,5-二甲基苯基)苯甲酰胺
  参考文献：
  名称：

  Anticonvulsant activity of 2- and 3-aminobenzanilides

  摘要：

  A series of 2- and 3-aminobenzanilides derived from ring-alkylated anilines were prepared and evaluated for anticonvulsant activity. These benzanilides were prepared in the course of studies designed to determine the relationship between the benzamide structure and anticonvulsant effects. The compounds were tested in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazole and in the rotorod assay for neurologic deficit. The 3-aminobenzanilide derived from 2,6-dimethylaniline, 21, was the most potent anti-MES compound, with an ED50 of 13.48 mg/kg and a protective index of 21.11 (PI = TD50/ED50). The activity profile for 21 compares favorably with that for phenobarbital and phenytoin.

  DOI：

  10.1021/jm00158a038
• 作为产物：
  描述：

  3,5-二甲基苯基异氰酸酯 在 potassium fluoride 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 N-(3,5-二甲基苯基)-3-硝基苯甲酰胺
  参考文献：
  名称：

  Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

  摘要：

  N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

  DOI：

  10.1021/acs.orglett.5b03061

文献信息

• [EN] PROCESS FOR DIRECT AMIDATION OF AMINES VIA RH(I)-CATALYZED ADDITION OF BOROXINES<br/>[FR] PROCÉDÉ D'AMIDATION DIRECTE D'AMINES PAR AJOUT DE BOROXINES CATALYSÉ AU RH(I)
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2017044043A1

  公开（公告）日：2017-03-16

  This invention relates to a process for making an amide by directly reacting a ferf-butyloxycarbonyl or carboxybenzyl N substituted amine with a boroxine derivative in the presence of a rhodium(l) catalyst, in the presence of a solvent an optionally in the presence of a base. The process provides means to react protected amines to amides using th boroganic reagent without the deprotection of an amine such that it can be directly converted from protected form in on step, and results in good yields in amide formation even for sterically hindered amines. Potassium fluoride is the preferre base in the reaction run in dioxane. Typical rhodium catalysts that can be used include rhodium(l) complex monomer and dimers such as chloro(1,5-cyclooctadiene) rhodium(l) dimer ("[CI(cod)Rh]2") or bis(1,5-cyclooctadiene)rhodium(l trifluoromethanesulfonate ("(cod)2Rh(OTf)").

  这项发明涉及一种通过在铑（Ⅰ）催化剂存在下，在溶剂的存在下和/或在碱的存在下，直接将ferf-丁氧羰基或羧基苄基N-取代胺与硼氧化物衍生物反应，从而制备酰胺的方法。该过程提供了一种反应受保护胺制备酰胺的手段，使用硼有机试剂而无需去保护胺，使得它可以直接从受保护形式转化为酰胺，即使对于立体位阻胺，也能在酰胺形成中获得良好产率。在二氧六环中运行的反应中，氟化钾是首选碱。可用的典型铑催化剂包括铑（Ⅰ）配合物单体和二聚体，如氯代（1,5-环辛二烯）铑（Ⅰ）二聚体（"[CI(cod)Rh]2"）或双（1,5-环辛二烯）铑（Ⅰ）三氟甲磺酸盐（"(cod)2Rh(OTf)"）。
• Copper(<scp>i</scp>)-catalyzed amidation reaction of organoboronic esters and isocyanates
  作者：Tedrick Thomas Salim Lew、Diane Shu Wen Lim、Yugen Zhang

  DOI：10.1039/c5gc01374g

  日期：——

  A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using ligand-free copper(I) catalyst. The reaction system demonstrated broad substrate...

  使用不含配体的铜（I）催化剂已经完成了一种简单有效的方法，由易于获得的有机硼酸酯和异氰酸酯制备酰胺。反应体系显示出广泛的底物...
• CLARK C. R.; LING CHING-MING; SANSOM R. T., J. MED. CHEM., 29,(1986) N 8, 1534-1537
  作者：CLARK C. R.、 LING CHING-MING、 SANSOM R. T.

  DOI：——

  日期：——