(2,5-Dioxopyrrolidin-1-yl) 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoate | 412301-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2,5-Dioxopyrrolidin-1-yl) 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoate
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoate
• CAS: 412301-56-5
• 化学式: C₂₃H₂₈F₃N₃O₅
• 分子量: 483.488
• InChiKey: NZMCGCOWHXOMJW-UHFFFAOYSA-N

物化性质

• 沸点：
  545.3±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2,5-Dioxopyrrolidin-1-yl) 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoate 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到2,5-dioxopyrrolidin-1-yl 11-{2-iodo-5-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenoxy}undecanoate
  参考文献：
  名称：

  Simple method for the introduction of iodo-label on (3-trifluoromethyl) phenyldiazirine for photoaffinity labeling

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2006.03.068
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-3-(三氟甲基)双吖丙啶 在 盐酸 、 sodium hydroxide 、 三溴化硼 、 四丁基碘化铵 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 11-[3-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]undecanoate
  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

• 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 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.