4-叠氮基-2,3,5,6-四氟苯甲酰胺 | 122616-98-2

• 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: 4-叠氮基-2,3,5,6-四氟苯甲酰胺
• 中文别名: 4-叠氮-2,3,5,6-四氟苯酰胺
• 英文名称: 4-azidotetrafluorobenzamide
• 英文别名: 4-Azido-2,3,5,6-tetrafluorobenzamide
• CAS: 122616-98-2
• 化学式: C₇H₂F₄N₄O
• mdl: MFCD03701127
• 分子量: 234.113
• InChiKey: CRAAAVAALQAHLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-叠氮基-2,3,5,6-四氟苯甲酰胺 在 sodium peroxide 作用下， 以 水 为溶剂， 反应 42.0h， 以64%的产率得到4-叠氮基-2,3,5,6-四氟苯甲酸
  参考文献：
  名称：

  New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides

  摘要：

  DOI：

  10.1021/jo00298a048
• 作为产物：
  描述：

  五氟苯腈 在 sodium hydroxide 、 双氧水 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以18%的产率得到4-叠氮基-2,3,5,6-四氟苯甲酰胺
  参考文献：
  名称：

  New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides

  摘要：

  DOI：

  10.1021/jo00298a048

文献信息

• Functionalized Perfluorophenyl Azides: New Reagents for Photoaffinity Labeling
  作者：John F.W. Keana、Sui Xiong Cai

  DOI：10.1016/s0022-1139(00)81644-9

  日期：1989.4

  Several substituted perfluorophenyl azides capable of attachment to other molecules by an acylation reaction were synthesized for use as photoaffinity labeling reagents.

  合成了几种能够通过酰化反应与其他分子连接的取代全氟苯基叠氮化物，用作光亲和标记试剂。
• Targeted activation in localized protein environments via deep red photoredox catalysis
  作者：Nicholas Eng Soon Tay、Keun Ah Ryu、John L. Weber、Aleksandra K. Olow、David C. Cabanero、David R. Reichman、Rob C. Oslund、Olugbeminiyi O. Fadeyi、Tomislav Rovis

  DOI：10.1038/s41557-022-01057-1

  日期：2023.1

  (λ = 660 nm) photoredox catalysis and its use in photocatalysed proximity labelling. We demonstrate that aryl azides are converted to triplet nitrenes via a redox-centric mechanism and show that its spatially localized formation requires both red light and a photocatalyst-targeting modality. This technology was applied in different colon cancer cell systems for targeted protein environment labelling of epithelial

  化学生物学中最先进的光活化策略提供了生物过程的时空控制和可视化。然而，使用高能光 ( λ < 500 nm) 进行底物或光催化剂敏化可能会导致光活性小分子探针的背景激活，并降低其在复杂生物环境中的功效。在这里，我们描述了通过深红光（ λ = 660 nm）光氧化还原催化靶向芳基叠氮化物活化的发展及其在光催化邻近标记中的应用。我们证明芳基叠氮化物通过氧化还原中心机制转化为三线态氮宾，并表明其空间局部形成需要红光和光催化剂靶向模式。该技术应用于不同结肠癌细胞系统中，对上皮细胞粘附分子（EpCAM）进行靶向蛋白质环境标记。我们鉴定了一小部分与 EpCAM 具有先前已知和未知关联的蛋白质，包括 CDH3，这是一种与 EpCAM 具有高肿瘤选择性表达的临床相关蛋白质。
• Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin
  作者：Raghoottama S. Pandurangi、Przemyslaw Lusiak、Robert R. Kuntz、Wynn A. Volkert、Jacek Rogowski、Matthew S. Platz

  DOI：10.1021/jo981458a

  日期：1998.11.1

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.
• Retention of Inhibitory Potency of an ACE Inhibitor Conjugated with Rh(III) and Pd(II) (Iminophosphorano)phosphines. Synthesis and X-ray Structural Investigations
  作者：Raghoottama S. Pandurangi、Kattesh V. Katti、Loreen Stillwell、Charles L. Barnes

  DOI：10.1021/ja9802403

  日期：1998.11.1

  Succinimido, amido, and ester functionalized tetrafluoroaryl azides selectively oxidize bisdiphenylphosphinomethane at one of the P(III) centers giving (iminophosphorano)phosphines 6, 7, and 8 respectively in high yields. Succinimido functionalized perfluoroaryl azido (iminophosphorano)phosphine is attached to angiotensin converting enzyme (ACE) inhibitor, lisinopril at one end, leaving the other end for chelation to Rh(III) and Pd(II) precursors including radioactive analogues establishing the hetero-bifunctionality for potential in vivo tracking of the radiotracer. The measurement of inhibitory potency of lisinopril-metal conjugates (Rh and Pd), modified through the primary amine reveals an increase in inhibitory potency, although small, retaining the target potential of native lisinopril toward specific biological sites. However, direct complexation utilizing the carboxylic groups of lisinopril with a Cu precursor resulted in the reduction of inhibitory potency from nM to mu M levels rendering it less useful for applications as an ACE inhibitor. Single-crystal X-ray structural investigation of the Rh(III) perfluoroaryl (iminophosphorano)phosphine complex 12 shows a distorted mer octahedral configuration with two ligands per metal center and only one of the phosphiniminato nitrogen atom coordinating to the metal. Pd(II) complex 18 reveals that the metal is bound to the iminato nitrogen atom and the P(III) center via cis disposition to form a five-membered ring. X-ray data for 12: triclinic, P-l, 11.570 (6) Angstrom b = 13.668 Angstrom (7) c = 20.709 (10) Angstrom, alpha = 86.068 (10), beta = 83.774 (10), gamma = 83.503 (10) a = 3229.6 (3) Angstrom(3), Z= 2, R = 0.028, R-w, 0.050. X-ray data for 18: triclinic, P-1, a = 11.457 (3) Angstrom, b = 12.223 (3) Angstrom, c = 13.219 (4) Angstrom, alpha = 89.98 (20), beta = 73.710 (20), gamma = 69.980 (20), V = 1665.7 (8) Angstrom(3), Z = 2, R = 0.024, R-w = 0.031.
• KEANA, JOHN F. W.;CAI, SUI XIONG, J. FLUOR. CHEM., 43,(1989) N, C. 151-154
  作者：KEANA, JOHN F. W.、CAI, SUI XIONG

  DOI：——

  日期：——