2-{2-[(9-butoxy-5,6-didehydro-11,12-dihydrodibenzo[a,e][8]annulen-2-yl)oxy]ethoxy}ethyl {2-[2-(2-{[5-(2-oxohexahydro-1H-thieno-[3,4-d]imidazol-4-yl)pentanoyl]amino}ethoxy)ethoxy]ethyl} carbamate | 1191419-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 2-{2-[(9-butoxy-5,6-didehydro-11,12-dihydrodibenzo[a,e][8]annulen-2-yl)oxy]ethoxy}ethyl {2-[2-(2-{[5-(2-oxohexahydro-1H-thieno-[3,4-d]imidazol-4-yl)pentanoyl]amino}ethoxy)ethoxy]ethyl} carbamate
• 英文别名: 2-[2-[(15-butoxy-6-tricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-ynyl)oxy]ethoxy]ethyl N-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethyl]carbamate
• CAS: 1191419-18-7
• 化学式: C₄₁H₅₆N₄O₉S
• 分子量: 780.983
• InChiKey: WFANFBQEDUEDMO-UZGNFBRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  55
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  180
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-{2-[(9-butoxy-5,6-didehydro-11,12-dihydrodibenzo[a,e][8]annulen-2-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate 、 N-生物素-3,6-二氧杂辛烷-1,8-二胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以13%的产率得到2-{2-[(9-butoxy-5,6-didehydro-11,12-dihydrodibenzo[a,e][8]annulen-2-yl)oxy]ethoxy}ethyl {2-[2-(2-{[5-(2-oxohexahydro-1H-thieno-[3,4-d]imidazol-4-yl)pentanoyl]amino}ethoxy)ethoxy]ethyl} carbamate
  参考文献：
  名称：

  Selective Labeling of Living Cells by a Photo-Triggered Click Reaction

  摘要：

  Phototriggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (Phi(355) = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based phototriggered click chemistry offers exciting opportunities to label living organisms in a temporally and spatially controlled manner and may facilitate the preparation of microarrays.

  DOI：

  10.1021/ja9054096

文献信息

• Selective Labeling of Living Cells by a Photo-Triggered Click Reaction
  作者：Andrei A. Poloukhtine、Ngalle Eric Mbua、Margreet A. Wolfert、Geert-Jan Boons、Vladimir V. Popik

  DOI：10.1021/ja9054096

  日期：2009.11.4

  Phototriggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (Phi(355) = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based phototriggered click chemistry offers exciting opportunities to label living organisms in a temporally and spatially controlled manner and may facilitate the preparation of microarrays.