1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazole | 1158815-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazole
• 英文别名: 1-benzyl-8,9-dihydro-1Hdibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazole
• CAS: 1158815-73-6
• 化学式: C₂₃H₁₉N₃
• 分子量: 337.424
• InChiKey: BONCFLDMJWEPLG-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  577.9±53.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5,6-didehydro-11,12-dihydrodibenzo[a,e]cyclooctene 、 苄基叠氮 在 三苯基膦 作用下， 以 氘代甲醇 为溶剂， 反应 1.0h， 以88%的产率得到1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazole
  参考文献：
  名称：

  使用2,6-二氯苯基叠氮化物衍生物的Staudinger反应可形成牢固的氮杂内酯，适用于活细胞的生物结合†

  摘要：

  使用缺乏电子的芳香族叠氮化物（例如2,6-二氯苯基叠氮化物）和三芳基膦之间的斯托丁格反应，可以有效地形成水和空气稳定的氮杂酰基。该反应进行迅速，已成功应用于活细胞中蛋白质的化学修饰。

  DOI：

  10.1039/c8cc00179k

文献信息

• Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions
  作者：Suguru Yoshida、Kimiyuki Kanno、Isao Kii、Yoshihiro Misawa、Masatoshi Hagiwara、Takamitsu Hosoya

  DOI：10.1039/c8cc01195h

  日期：——

  A facile strategy for the synthesis of trifunctional molecules involving three sequential selective triazole-forming reactions is proposed. This method exploits three kinds of mechanistically different azido-type-selective cycloadditions. Three different azidophiles could be efficiently connected to a triazido platform molecule with three types of azido groups in a consecutive manner, which rendered

  提出了一种容易的合成三官能分子的策略，涉及三个连续的选择性三唑形成反应。该方法利用了三种机械上不同的叠氮基类型选择性环加成反应。可以以连续的方式将三种不同的亲氮化合物有效地连接到具有三种类型的叠氮基团的三叠氮平台分子上，这使得实用的三官能分子易于获得。
• Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes
  作者：Craig S. McKay、Joseph Moran、John Paul Pezacki

  DOI：10.1039/b921630h

  日期：——

  Strain-promoted cycloadditions of nitrones with cyclooctynes (k2 = 1.5 M−1 s−1 at 25 °C) are up to 25 times more rapid than comparable reactions of azides.

  腈与环辛炔的应变促进环加成反应（25 °C时k2 = 1.5 M-1 s-1）比叠氮化物的类似反应快25倍。
• Selective strain-promoted azide–alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold
  作者：Keisuke Adachi、Tomohiro Meguro、Yuki Sakata、Kazunobu Igawa、Katsuhiko Tomooka、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1039/d0cc04606j

  日期：——

  Complexation of bicyclo[6.1.0]nonynes with a cationic silver or gold salt results in protection from a click reaction with azides. The cycloalkyne protection using the silver or gold salt enables selective strain-promoted azide–alkyne cycloadditions of diynes keeping the bicyclo[6.1.0]nonyne moiety unreacted.

  双环[6.1.0]壬炔与阳离子银或金盐的络合可防止与叠氮化物发生点击反应。使用银盐或金盐进行的环炔保护可选择性地促进二炔的叠氮化物-炔环加成反应，从而使双环[6.1.0] nonyne部分未反应。
• Facile assembly of three cycloalkyne-modules onto a platform compound bearing thiophene <i>S</i>,<i>S</i>-dioxide moiety and two azido groups
  作者：Tomohiro Meguro、Yuki Sakata、Takamoto Morita、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1039/d0cc01810d

  日期：——

  An efficient method to assemble three cycloalkyne-modules onto a platform compound bearing a thiophene S,S-dioxide moiety and two azido groups has been developed. The sequential reactions without catalysis or additives enabled the facile preparation of trifunctional molecules by a simple procedure. One-pot assembly was also achieved using the platform and three cycloalkynes.

  已经开发了一种将三个环炔烃模块组装到带有噻吩S，S-二氧化物部分和两个叠氮基的平台化合物上的有效方法。没有催化剂或添加剂的顺序反应使得可以通过简单的程序轻松制备三官能分子。使用该平台和三个环炔烃也可以实现一锅组装。
• A Bioorthogonal Ligation Enabled by Click Cycloaddition of<i>o</i>-Quinolinone Quinone Methide and Vinyl Thioether
  作者：Qiang Li、Ting Dong、Xiaohui Liu、Xiaoguang Lei

  DOI：10.1021/ja401989p

  日期：2013.4.3

  There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.