11-{3-[3-(Trifluoromethyl)-3H-diaziren-3-yl]phenoxy}undecanoic acid | 412301-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11-{3-[3-(Trifluoromethyl)-3H-diaziren-3-yl]phenoxy}undecanoic acid
• 英文别名: 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoic acid
• CAS: 412301-55-4
• 化学式: C₁₉H₂₅F₃N₂O₃
• 分子量: 386.414
• InChiKey: HAGLFWXYLMDTMB-UHFFFAOYSA-N

物化性质

• 沸点：
  478.7±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11-{3-[3-(Trifluoromethyl)-3H-diaziren-3-yl]phenoxy}undecanoic acid 在 三氯化铝 、 三乙基(硅烷-d) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 11-[2-[1-13CD2]ethyl-5-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]oxyundecanoic acid
  参考文献：
  名称：

  简单合成氘和13C标记的三氟甲基苯基重氮衍生物作为质谱的稳定同位素标记。

  摘要：

  报道了具有稳定同位素标记的三氟甲基二嗪胺的合成。我们发现，使用市售的稳定同位素试剂进行的弗瑞德-克来福特酰化和芳基羰基还原为亚甲基均被用于合成二叠氮基脂肪酸衍生物。稳定的同位素标记的二嗪啉对于通过质谱鉴定结合位点可能很有价值。

  DOI：

  10.1248/cpb.52.1385
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-3-(三氟甲基)双吖丙啶 在 sodium hydroxide 、 三溴化硼 、 四丁基碘化铵 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 11-{3-[3-(Trifluoromethyl)-3H-diaziren-3-yl]phenoxy}undecanoic acid
  参考文献：
  名称：

  Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide

  摘要：

  A versatile synthesis of diazirine-based photoreactive fatty acid analogues is reported. The key step is phenoxy alkylation of diazirine with halo alkyl acid esters. The conditions described will be acceptable for the synthesis of various alkyl-length derivatives. The fatty acid derivatives are acceptors for reverse reactions of sphingolipid ceramide N-deacylase (SCDase), which catalyzes the condensation of psychosine and fatty acids to form photoreactive galactosylceramide. The photoreactive galactosylceramide can also be prepared with chemical synthesis, condensation of psychosine and fatty acid succinimidyl ester, and is recognized with anti-GarCer antibody both before and after irradiation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00669-2

文献信息

• Simple method for the introduction of iodo-label on (3-trifluoromethyl) phenyldiazirine for photoaffinity labeling
  作者：Makoto Hashimoto、Yuhi Kato、Yasumaru Hatanaka

  DOI：10.1016/j.tetlet.2006.03.068

  日期：2006.5

  A simple and mild method was developed for the introduction of iodo-label on (3-trifluoromethyl) phenyidiazirine (TPD) aromatic ring in the presence of three membered diazirine ring. An iodination protocol, I-2-BTI in CH3CN, was found to be effective even though affinity ligands are pre-installed. (c) 2006 Elsevier Ltd. All rights reserved.
• A novel biotinylated diazirinyl ceramide analogue for photoaffinity labeling
  作者：Makoto Hashimoto、Yasumaru Hatanaka

  DOI：10.1016/j.bmcl.2007.11.071

  日期：2008.1

  A novel photoreactive ceramide analogue, which contains (3-trifluoromethyl)phenyldiazirinyl lipid and biotinylated sphingosine, was synthesized. The probe was recognized as an antigen by anti-ceramide antibody and as a substrate for sphingolipid ceramide N-deacylase. These results indicate that the probe may be useful as a photoaffinity-biotinylating agent in sphingolipid studies. (c) 2007 Elsevier Ltd. All rights reserved.
• Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide
  作者：Makoto Hashimoto、Yasumaru Hatanaka、Kensuke Nabeta

  DOI：10.1016/s0960-894x(01)00669-2

  日期：2002.1

  A versatile synthesis of diazirine-based photoreactive fatty acid analogues is reported. The key step is phenoxy alkylation of diazirine with halo alkyl acid esters. The conditions described will be acceptable for the synthesis of various alkyl-length derivatives. The fatty acid derivatives are acceptors for reverse reactions of sphingolipid ceramide N-deacylase (SCDase), which catalyzes the condensation of psychosine and fatty acids to form photoreactive galactosylceramide. The photoreactive galactosylceramide can also be prepared with chemical synthesis, condensation of psychosine and fatty acid succinimidyl ester, and is recognized with anti-GarCer antibody both before and after irradiation. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Simple Synthesis of Deuterium and 13C Labeled Trifluoromethyl Phenyldiazirine Derivatives as Stable Isotope Tags for Mass Spectrometry
  作者：Makoto Hashimoto、Yasumaru Hatanaka

  DOI：10.1248/cpb.52.1385

  日期：——

  The synthesis of trifluoromethyl diazirine with a stable isotope tag is reported. We found that both Friedel-Crafts acylation and reduction of aryl carbonyl to methylene, using commercially available stable-isotope reagents, were utilized for the synthesis of diazirinyl fatty acid derivatives. The stable isotope labeled diazirine may be valuable for identifying binding sites by mass spectrometry.

  报道了具有稳定同位素标记的三氟甲基二嗪胺的合成。我们发现，使用市售的稳定同位素试剂进行的弗瑞德-克来福特酰化和芳基羰基还原为亚甲基均被用于合成二叠氮基脂肪酸衍生物。稳定的同位素标记的二嗪啉对于通过质谱鉴定结合位点可能很有价值。