[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenoxy]acetic acid | 152565-36-1

• 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: [4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenoxy]acetic acid
• 英文别名: {4-[3-(trifluoromethyl)-1H-diaziren-3-yl]phenoxy}acetic acid；TFMAD
• CAS: 152565-36-1
• 化学式: C₁₀H₇F₃N₂O₃
• 分子量: 260.172
• InChiKey: JEOFTJBLRAQUOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenoxy]acetic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成
  参考文献：
  名称：

  Synthesis and Evaluation of a Photoactive Probe with a Multivalent Carbohydrate for Capturing Carbohydrate–Lectin Interactions

  摘要：

  Lectins are ubiquitous carbohydrate-binding proteins of nonimmune origin that are characterized by their specific recognition of defined monosaccharide or oligosaccharide structures. However, the use of carbohydrates to study lectin has been restricted by the weak binding affinity and noncovalent character of the interaction between carbohydrates and lectin. In this report, we designed and synthesized a multifunctional photoaffinity reagent composed of a trialkyne chain, a masked latent amine group, and a photoreactive 3-trifluoromethyl-3phenyl-diazirine group in high overall yield. Two well-defined chemistries, Huisgen-Sharpless click chemistry and amide bond coupling, were the key steps for installing the multivalent character and tag in our designed photoaffinity probe. The photolabeling results demonstrated that the designed probe selectively labeled the target lectin, RCA(120) (Ricinus communis Agglutinin), in an E. coli lysate and an asialoglycoprotein receptor (ASGP-R) on intact HepG2 cell membranes. Moreover, the probe also enabled the detection of weak protein protein interactions between RCA(120) and ovalbumin (OVA).

  DOI：

  10.1021/bc400306g
• 作为产物：
  描述：

  tert-butyl 2-(4-(2,2,2-trifluoroacetyl)phenoxy)acetate 在 吡啶 、 三异丙基硅烷 、 盐酸羟胺 、 氨 、 碘 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.34h， 生成 [4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenoxy]acetic acid
  参考文献：
  名称：

  A generic small-molecule microarray immobilization strategy

  摘要：

  Small-molecule microarrays are often limited by the requirement for each compound undergoing immobilization to contain a common functional group or by the need to prepare glass slides containing photo-reactive groups. Herein, we present a generic strategy that allows any compound library to be immobilized. This was achieved by printing a fluorous-tagged photo-reactive 3-aryl-3-trifluoromethyldiazirine, which undergoes non-selective insertion into compounds following UV-activation, onto fluorous-functionalized glass slides. The arrays could be reused following aqueous stripping and re-assessment of the compounds with the same protein or another target of interest. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.055