5-(azidomethyl)benzo[c][1,2,5]oxadiazole | 1196670-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5-(azidomethyl)benzo[c][1,2,5]oxadiazole
• 英文别名: 5-(Azidomethyl)-2,1,3-benzoxadiazole
• CAS: 1196670-48-0
• 化学式: C₇H₅N₅O
• 分子量: 175.15
• InChiKey: JGYRKDAWUWGNLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(azidomethyl)benzo[c][1,2,5]oxadiazole 、 {2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylprop-2-ynylammonium 在 copper(II) sulfate 、 维生素 C 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以100%的产率得到(1-benzo[1,2,5]oxadiazol-5-ylmethyl-1H-[1,2,3]triazol-4-ylmethyl)-{2-[(2-hexadecanoylamino-3-hydroxyoctadec-4-enyloxy)hydroxyphosphoryloxy]ethyl}dimethylammonium
  参考文献：
  名称：

  A Modular Synthesis of Alkynyl-Phosphocholine Headgroups for Labeling Sphingomyelin and Phosphatidylcholine

  摘要：

  A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and call be easily modified to introduce desired functional groups at the N-acyl chain. The targets accessible with this strategy provide a bioorthogonal handle for postsynthetic introduction of fluorophores or other labeling agents with aqueous phase chemistry. We report the synthesis of sphingomyelin derivatives that incorporate a fluorophore and an alkyne. The modified sphingolipids retain activity as substrates for sphingomyelinase, making these compounds viable probes of enzymatic activity. Importantly, the strategy allows modification of the lipid across the phosphodiester, making the alkyne a potential probe of sphingomyelinase activity.

  DOI：

  10.1021/jo901824h
• 作为产物：
  描述：

  5-溴甲基-2,1,3-苯并二唑 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 以82%的产率得到5-(azidomethyl)benzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  Identification of fluorogenic and quenched benzoxadiazole reactive chromophores

  摘要：

  The Sharpless-Meldal reaction was employed to generate triazole-substituted, alkynyl, azido and tri-azolyl-benzoxadiazole as well as nitro-benzoxadiazole fluorophores Linkage of the triazole to the benzoxadiazole ring at C4 gave chromophores which were fluorogenic, while attachment through NI resulted in quenching The 4-azalo-7-nitrobenzoxadiazole underwent a 470-fold decrease in quantum yield upon conversion to the triazole While, 5-ethynyl-benzoxadiazole exhibited a 48-fold enhancement of quantum yield upon formation of tnazole The modulating effects of solvent polarity, conjugation, and attachment point of the fluorochrome to the tnazole were examined (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.05.007

文献信息

• A Modular Synthesis of Alkynyl-Phosphocholine Headgroups for Labeling Sphingomyelin and Phosphatidylcholine
  作者：Mahendra S. Sandbhor、Jessie A. Key、Ileana S. Strelkov、Christopher W. Cairo

  DOI：10.1021/jo901824h

  日期：2009.11.20

  A general route to phospho- and sphingolipids that incorporate an alkyne in the phosphocholine headgroup is described. The strategy preserves the ammonium functionality of the phosphocholine and call be easily modified to introduce desired functional groups at the N-acyl chain. The targets accessible with this strategy provide a bioorthogonal handle for postsynthetic introduction of fluorophores or other labeling agents with aqueous phase chemistry. We report the synthesis of sphingomyelin derivatives that incorporate a fluorophore and an alkyne. The modified sphingolipids retain activity as substrates for sphingomyelinase, making these compounds viable probes of enzymatic activity. Importantly, the strategy allows modification of the lipid across the phosphodiester, making the alkyne a potential probe of sphingomyelinase activity.
• Identification of fluorogenic and quenched benzoxadiazole reactive chromophores
  作者：Jessie A. Key、Christopher W. Cairo

  DOI：10.1016/j.dyepig.2010.05.007

  日期：2011.1

  The Sharpless-Meldal reaction was employed to generate triazole-substituted, alkynyl, azido and tri-azolyl-benzoxadiazole as well as nitro-benzoxadiazole fluorophores Linkage of the triazole to the benzoxadiazole ring at C4 gave chromophores which were fluorogenic, while attachment through NI resulted in quenching The 4-azalo-7-nitrobenzoxadiazole underwent a 470-fold decrease in quantum yield upon conversion to the triazole While, 5-ethynyl-benzoxadiazole exhibited a 48-fold enhancement of quantum yield upon formation of tnazole The modulating effects of solvent polarity, conjugation, and attachment point of the fluorochrome to the tnazole were examined (C) 2010 Elsevier Ltd. All rights reserved.