3-[(4-aminophenyl)diazenyl]benzoic acid | 752929-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 3-[(4-aminophenyl)diazenyl]benzoic acid
• 英文别名: 3,4'-APB
• CAS: 752929-41-2
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: IAKILGDTLVGALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(4-aminophenyl)diazenyl]benzoic acid 、 2-(4-Dimethylamino-benzyliden)-acetessigsaeureethylester 在 lead(IV) tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以66%的产率得到2-acetyl-2-ethoxycarbonyl-1-[4-(3-carboxyphenylazo)phenyl]-3-(4-dimethylaminophenyl)aziridine
  参考文献：
  名称：

  Synthesis and QSAR modeling of 2-acetyl-2-ethoxycarbonyl-1-[4(4′-arylazo)-phenyl]-N,N-dimethylaminophenyl aziridines as potential antibacterial agents

  摘要：

  The present communication deals with the synthesis of a series of 2-acetyl-2-ethoxycarbonyl-1-[4(4'-arylazo)-phenyl]-N,N-dimethylaminophenyl aziridines. The compounds were synthesized in excellent yields (70-80%) and the structures were established on the basis of consistent IR, H-1 NMR and elemental analysis data. The purity has been ascertained by chromatographic resolution using acetic acid-toluene (6:4 v/v) as binary eluent. All the compounds have been tested for their antimicrobial activity against a representative panel of bacteria i.e. Bacillus subtilis, Escherichia coli, Pseudomonas diminuta and Staphylococcus aureus using azinomycin as reference drug. All the synthesized compounds were found to exhibit profound antimicrobial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.016
• 作为产物：
  描述：

  3-[(4-nitrophenyl)diazenyl]benzoic acid 在 sodium sulfide 、 水 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到3-[(4-aminophenyl)diazenyl]benzoic acid
  参考文献：
  名称：

  基于偶氮苯的ω-氨基酸及其相关结构单元：合成，性质及其在肽化学中的应用

  摘要：

  偶氮苯被广泛用作光敏材料开发的光引发剂。从文献已知的ω-氨基酸4,4'-APB 1a和4,4'-AMPB 2a开始，合成了间位取代的类似物，用于掺入肽和蛋白质。虽然4,4'-APB 1a需要特殊的化学合成肽，但Fmoc / t- Bu保护基策略适用于3,3'-APB 1b。通过制备具有结合基序pTyr-Val-Asn-Val的环状可光转换磷酸肽，证明了这种和其他新颖的偶氮苯ω-氨基酸的多功能性。还介绍了偶氮亚基和相应肽的光致变色性质。 偶氮化合物-氨基酸-肽-光开关-光致变色

  DOI：

  10.1055/s-0029-1217074

文献信息

• Synthesis and QSAR modeling of 2-acetyl-2-ethoxycarbonyl-1-[4(4′-arylazo)-phenyl]-N,N-dimethylaminophenyl aziridines as potential antibacterial agents
  作者：Pratibha Sharma、Ashok Kumar、Siya Upadhyay、Vinita Sahu、Jitendra Singh

  DOI：10.1016/j.ejmech.2008.02.016

  日期：2009.1

  The present communication deals with the synthesis of a series of 2-acetyl-2-ethoxycarbonyl-1-[4(4'-arylazo)-phenyl]-N,N-dimethylaminophenyl aziridines. The compounds were synthesized in excellent yields (70-80%) and the structures were established on the basis of consistent IR, H-1 NMR and elemental analysis data. The purity has been ascertained by chromatographic resolution using acetic acid-toluene (6:4 v/v) as binary eluent. All the compounds have been tested for their antimicrobial activity against a representative panel of bacteria i.e. Bacillus subtilis, Escherichia coli, Pseudomonas diminuta and Staphylococcus aureus using azinomycin as reference drug. All the synthesized compounds were found to exhibit profound antimicrobial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Azobenzene-Based ω-Amino Acids and Related Building Blocks: Synthesis, Properties, and Application in Peptide Chemistry
  作者：Karola Rück-Braun、Stefan Kempa、Beate Priewisch、Anja Richter、Sabine Seedorff、Lukas Wallach

  DOI：10.1055/s-0029-1217074

  日期：——

  from the literature-known ω-amino acids 4,4′-APB 1a and 4,4′-AMPB 2a, meta-substituted analogues were synthesized for the incorporation into peptides and proteins. While 4,4′-APB 1a requires special chemistry for peptide synthesis, an Fmoc/t-Bu protecting group strategy is applicable for 3,3′-APB 1b. The versatility of this and other novel azobenzene ω-amino acids is demonstrated by the preparation

  偶氮苯被广泛用作光敏材料开发的光引发剂。从文献已知的ω-氨基酸4,4'-APB 1a和4,4'-AMPB 2a开始，合成了间位取代的类似物，用于掺入肽和蛋白质。虽然4,4'-APB 1a需要特殊的化学合成肽，但Fmoc / t- Bu保护基策略适用于3,3'-APB 1b。通过制备具有结合基序pTyr-Val-Asn-Val的环状可光转换磷酸肽，证明了这种和其他新颖的偶氮苯ω-氨基酸的多功能性。还介绍了偶氮亚基和相应肽的光致变色性质。 偶氮化合物-氨基酸-肽-光开关-光致变色