(10-azidomethylanthracen-9-yl)methanol | 1019335-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (10-azidomethylanthracen-9-yl)methanol
• 英文别名: [10-(Azidomethyl)anthracen-9-yl]methanol
• CAS: 1019335-97-7
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: QMOQEOAKHNLYJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (10-azidomethylanthracen-9-yl)methanol 、 2-甲基-1-丁烯-3-炔 在 copper(I) sulfate 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 (10-((4-(prop-1-en-2-yl)-1H-1,2,3-triazol-1-yl)methyl)anthracen-9-yl)methanol
  参考文献：
  名称：

  A fluorogenic ‘click’ reaction of azidoanthracene derivatives

  摘要：

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.080
• 作为产物：
  描述：

  2-(1-anthracen-2-yl-1H-[1,2,3]triazol-4-yl)-ethanol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以83%的产率得到(10-azidomethylanthracen-9-yl)methanol
  参考文献：
  名称：

  A fluorogenic ‘click’ reaction of azidoanthracene derivatives

  摘要：

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.080

文献信息

• A novel rearrangement of fluorescent human thymidylate synthase inhibitor analogues in ESI tandem mass spectrometry
  作者：Yi Chen、Céline Le Droumaguet、Kai Li、William E. Cotham、Norman Lee、Mike Walla、Qian Wang

  DOI：10.1016/j.jasms.2009.11.004

  日期：2010.3.1

  Cu(I) catalyzed alkyne-azide cycloaddition reaction was employed to synthesize a series of anthracene-based human thymidylate synthase (hTS) inhibitor analogues. The triazolo-anthracene derivatives were characterized by ESI-MS/MS and a novel rearrangement reaction in ESI-MS/MS was observed. The mechanism is proposed whereby the protonated triazolo-anthracene derivative forms a carbocation, and then

  Cu(I) 催化的炔-叠氮化物环加成反应用于合成一系列基于蒽的人胸苷酸合酶 (hTS) 抑制剂类似物。三唑并蒽衍生物通过 ESI-MS/MS 进行表征，并在 ESI-MS/MS 中观察到新的重排反应。提出的机制是质子化的三唑并蒽衍生物形成碳正离子，然后碳正离子亲电攻击蒽部分，导致形成重排离子。此外，碳正离子更倾向于通过亲电取代机制攻击 γ 位置而不是蒽部分的 α 或 β 位置。
• MODULAR CONSTRUCTION OF LIPOPHOSPHOLIPIDS
  申请人：Haelters Jean-Pierre

  公开号：US20130178609A1

  公开（公告）日：2013-07-11

  The present invention relates to fluorescent and/or targeting lipophilic compounds having the general formula (R1O)(R2O)P(O)—R3-R4-R5 wherein R1 and R2 are each independently a linear or branched, saturated or unsaturated C2-C24 alkyl, or a linear or branched, saturated or unsaturated C2-C24 monoalkenyl or polyalkenyl, the polyalkenyl having from 2 to 4 double bonds, or a linear or branched, saturated or unsaturated C2-C24 monoalkinyl or polyalkinyl, the polyalkinyl having from 2 to 4 triple bonds; R3 is selected from 0, S, —C(R6)2-, —CH(R7)-, —C(S)—N(R6)-, —CH(SR7)-S—S— or —N(R6)- wherein R6 is a hydrogen atom or a C1-C4 alkyl, and R7 is a C1-C4 alkyl; R4 comprises at least one junction function and at least one linker; and R5 is at least one chemical fluorescent group or at least one targeting group. Methods for preparing said lipophilic compounds are also disclosed.

  本发明涉及具有一般式（R1O）（R2O）P（O）-R3-R4-R5的荧光和/或靶向性亲脂性化合物，其中R1和R2各自独立地为线性或支链的饱和或不饱和的C2-C24烷基，或线性或支链的饱和或不饱和的C2-C24单烯基或多烯基，多烯基具有2至4个双键，或线性或支链的饱和或不饱和的C2-C24单炔基或多炔基，多炔基具有2至4个三键；R3从0，S，-C（R6）2-，-CH（R7）-，-C（S）-N（R6）-，-CH（SR7）-S-S-或-N（R6）-中选择，其中R6是氢原子或C1-C4烷基，R7是C1-C4烷基；R4包括至少一个连接功能和至少一个连接基；R5至少是一个化学荧光基团或至少一个靶向基团。本发明还公开了制备上述亲脂性化合物的方法。
• A fluorogenic ‘click’ reaction of azidoanthracene derivatives
  作者：Fang Xie、Krishnamoorthy Sivakumar、Qingbing Zeng、Michael A. Bruckman、Blake Hodges、Qian Wang

  DOI：10.1016/j.tet.2008.01.080

  日期：2008.3

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.