N-(2,6-dinitrophenyl)-β-alanine

• 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-dinitrophenyl)-β-alanine
• 英文别名: N-(2,6-dinitrophenyl)-3-aminopropanoic acid；3-(2,6-Dinitroanilino)propanoic acid；3-(2,6-dinitroanilino)propanoic acid
• 化学式: C₉H₉N₃O₆
• 分子量: 255.187
• InChiKey: WOUJTWWQPMSJDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2,6-dinitrophenyl)-β-alanine 在 potassium carbonate 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 0.18h， 以31 mg的产率得到2-methyl-7-nitro-1H-benzimidazole 3-oxide
  参考文献：
  名称：

  Preparation of benzimidazole N-oxides by a two-step continuous flow process

  摘要：

  A continuous flow process for the synthesis of nitrobenzimidazole N-oxides from 2,6-dinitrochlorobenzene and amines or amino acids is reported. The process, performed in a two-step sequence, is faster than previously reported batch processes and avoids some of the isolation and purification steps.

  DOI：

  10.1007/s10593-017-1992-1
• 作为产物：
  描述：

  2,6-二硝基氯苯 、 β-丙氨酸 以 乙醇 为溶剂， 反应 0.42h， 生成 N-(2,6-dinitrophenyl)-β-alanine
  参考文献：
  名称：

  Preparation of benzimidazole N-oxides by a two-step continuous flow process

  摘要：

  A continuous flow process for the synthesis of nitrobenzimidazole N-oxides from 2,6-dinitrochlorobenzene and amines or amino acids is reported. The process, performed in a two-step sequence, is faster than previously reported batch processes and avoids some of the isolation and purification steps.

  DOI：

  10.1007/s10593-017-1992-1

文献信息

• FromN-(dinitrophenyl) amino acids to benzimidazoleN-oxides. Synthesis, kinetics and mechanism
  作者：Elba I. Buján、María Laura Salum

  DOI：10.1002/poc.1017

  日期：2006.3

  Several benzimidazole N-oxide derivatives were synthesized in very good yields by heating under reflux the corresponding N-(2,4- or 2,6-dinitrophenyl) amino acid derivative with NaOH in 60% 1,4-dioxane–H2O. The N-oxides obtained from glycine and α- and β-alanine derivatives lost the carboxylic group. The observed rate constant for the reaction of N-(2,4-dinitrophenyl) glycine (2a) in 10% 1,4-dioxane–H2O

  通过在60％1,4-二恶烷–H 2 O中用NaOH加热回流相应的N-（2,4-或2,6-二硝基苯基）氨基酸衍生物，可以以很高的收率合成几种苯并咪唑N-氧化物衍生物。由甘氨酸以及α-和β-丙氨酸衍生物获得的N-氧化物失去了羧基。N-（2,4-二硝基苯基）甘氨酸（2a）在10％1,4-二恶烷-H 2 O中反应生成5-硝基-1 H-苯并咪唑-3-氧化物（4a）的观察到的速率常数在[NaOH]上是一阶；二阶速率常数为k N = 1.7×10 -3 M -1  s -1。提出的机理包括形成N-亚烷基2-亚硝基苯胺型中间体作为速率确定步骤。版权所有©2006 John Wiley＆Sons，Ltd.
• Atropisomeric Properties of 5N‐Benzoyl‐1,5‐benzodiazepin‐2‐ones: Substituent Effects on Rotation around the Ar–N(CO) Axis
  作者：Kaoru Funaki、Hidetsugu Tabata、Hiromi Inyaku、Mizuki Mori、Tomohiko Tasaka、Hideyo Takahashi、Hideaki Natsugari、Tetsuta Oshitari

  DOI：10.1002/ejoc.202400343

  日期：——

  Atropisomeric properties of 5N-benzoyl-1,5-benzodiazepin-2-one with two Ar−N(CO) axes moving like gears were investigated. The rotational barrier (ΔG≠) of the axes was strongly influenced by the electronic effect of the p-substituent on benzoyl, and the electron-withdrawing group (EWG) increased the stability of the axes. The ΔG≠ values were linearly correlated with the electronic effect (the Hammett

  研究了具有两个像齿轮一样移动的 Ar−N(CO) 轴的 5N-苯甲酰基-1,5-苯二氮卓-2-酮的阻转异构性质。轴的旋转势垒(ΔG ≠ )受到苯甲酰基上p-取代基的电子效应的强烈影响，吸电子基团(EWG)增加了轴的稳定性。 ΔG ≠ 值与官能团的电子效应（Hammett σ 常数）线性相关。
• TRICYCLIC COMPOUNDS HAVING CORTICOTROPIN-RELEASING FACTOR ANTAGONISTIC ACTIVITY AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2240485A1

  公开（公告）日：2010-10-20
• [EN] TRICYCLIC COMPOUNDS HAVING CORTICOTROPIN-RELEASING FACTOR ANTAGONISTIC ACTIVITY AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] COMPOSÉS TRICYCLIQUES PRÉSENTANT UNE ACTIVITÉ ANTAGONISTE ENVERS LE FACTEUR DE LIBÉRATION DE LA CORTICOTROPINE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2009093747A1

  公开（公告）日：2009-07-30

  There is provided a compound of the formula (I') : wherein X is a nitrogen or CRx, Rx is a hydrogen, etc., R1 is an optionally substituted hydrocarbon group, etc., R2 is an optionally substituted hydrocarbon group, etc., ring A is 5- to -8-membered heterocyclic ring, etc., and each of Y1,. Y2 and Y3 is an optionally substituted carbon or a nitrogen, etc.; or 'a salt thereof or a prodrug thereof., which have CRF receptor antagonistic activity and use thereof.
• Preparation of benzimidazole N-oxides by a two-step continuous flow process
  作者：Fabrizio Politano、Elba I. Buján、Nicholas E. Leadbeater

  DOI：10.1007/s10593-017-1992-1

  日期：2016.11

  A continuous flow process for the synthesis of nitrobenzimidazole N-oxides from 2,6-dinitrochlorobenzene and amines or amino acids is reported. The process, performed in a two-step sequence, is faster than previously reported batch processes and avoids some of the isolation and purification steps.