4-butoxy-9-hydroxy-6,7-dihydro-1H-dibenzo[a,e]cyclopropa[c][8]annulen-1-one | 1239744-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-butoxy-9-hydroxy-6,7-dihydro-1H-dibenzo[a,e]cyclopropa[c][8]annulen-1-one
• 英文别名: 8-Butoxy-15-hydroxytetracyclo[11.4.0.02,4.05,10]heptadeca-1(13),2(4),5(10),6,8,14,16-heptaen-3-one
• CAS: 1239744-64-9
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: LOEWAMGXPXPADV-UHFFFAOYSA-N

物化性质

• 沸点：
  578.9±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-butoxy-9-hydroxy-6,7-dihydro-1H-dibenzo[a,e]cyclopropa[c][8]annulen-1-one 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 16.33h， 生成
  参考文献：
  名称：

  PM-IRRAS研究Au SAMs光点击衍生化。

  摘要：

  在这项工作中，我们提出了一个干净的一步法，使用光激活的点击化学方法修饰金上自组装单分子层（SAMs）的头基。首先通过自组装将巯基化的，环丙烯酮笼蔽的应变炔前体官能化到平坦的金基底上。环丙烯酮SAM暴露于UVA光会引发环丙烯酮部分的有效光化学脱羰作用，从而揭示能够经受界面应变促进的炔-叠氮化物环加成（SPAAC）的应变炔烃。用一系列疏水性不同的叠氮化物模型对辐照的SAM进行衍生化，以证明该化学体系用于修饰和微调金基底表面化学性质的一般性。在每个步骤中，通过偏振调制红外反射吸收光谱仪（PM-IRRAS）对SAM进行表征，以确认成功的功能化和反应性。此外，为了展示该方法与生化应用的兼容性，对环丙烯酮SAM进行了辐照，并用含叠氮化物的细胞粘附肽进行了修饰，以促进人成纤维细胞的粘附，然后通过活细胞荧光显微镜成像。因此，本文报道的“ photoclick”方法代表了一种改进的，通用的，无催化剂的方案，

  DOI：

  10.1021/acs.langmuir.9b03782
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 4-butoxy-9-hydroxy-6,7-dihydro-1H-dibenzo[a,e]cyclopropa[c][8]annulen-1-one
  参考文献：
  名称：

  在小型水溶性金纳米颗粒上“光亮单击”光诱导的炔烃的界面暴露

  摘要：

  在这项研究中，我们报告了3nm纳米水溶性金纳米颗粒（AuNPs）的设计，合成和表征，这些纳米颗粒具有被环丙烯酮掩盖的应变炔烃部分，能够在暴露于叠氮化物后经历界面应变促进环加成（i-SPAAC）的作用。 UV‐A灯。应变炔烃前体通过硫醇修饰的环丙烯酮掩蔽的二苯并环辛炔（photoDIBO）配体的直接配体交换而结合到AuNPs上。这些photoDIBO-AuNPs的特征是11 H NMR，IR和UV / Vis光谱，以及透射电子显微镜（TEM）和热重分析（TGA），并对修饰的程度进行了定量。在用UV-A光照射后，photoDIBO-AuNPs通过光化学脱羰作用对母体应变炔进行了高效且定量的再生，从而获得了DIBO衍生的AuNPs。发现DIBO-AuNPs通过界面应变促进的炔叠氮化物环丙二酮（i-SPAAC）与叠氮化苄反应，可以干净快速地反应（k = 5.3×10 -2  m -1  s -1）

  DOI：

  10.1002/chem.201603398

文献信息

• Cyclopropenones and the Photochemical Generation of Cyclic Alkynes Therefrom
  申请人：Popik Vladimir V.

  公开号：US20100210854A1

  公开（公告）日：2010-08-19

  Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.

  环状炔烃（例如，二苯并环辛烯等）可以从环丙酮烯光化学地生成，如本文所披露的。这些环状炔烃可以与具有炔烃反应基团（例如，“点击”反应中的偶氮基团）的材料发生反应（例如，在原位）。在优选实施例中，环状炔烃的生成和反应可以在无催化剂（例如，Cu(I)）的情况下进行。这些反应可以用于例如，用于选择性标记通过含有偶氮基团表面单糖代谢修饰的活细胞，或用于光导向表面图案。
• CYCLOPROPENONES AND THE PHOTOCHEMICAL GENERATION OF CYCLIC ALKYNES THEREFROM
  申请人：POPIK VLADIMIR V.

  公开号：US20120295318A1

  公开（公告）日：2012-11-22

  Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.

  环状炔烃（例如，二苯并环辛炔烃等）可以从环丙酮中进行光化学合成，如本文所述。环状炔烃可以与具有炔基反应性基团的材料（例如“点击”反应中的偶氮基团）反应（例如原位反应）。在优选实施方式中，生成和反应环状炔烃可以在无催化剂（例如Cu（I））的情况下进行。例如，这些反应可以用于选择性标记代谢修饰有含偶氮基团表面单糖的活细胞，或用于光驱动表面图案化。
• 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.
• High Density Orthogonal Surface Immobilization via Photoactivated Copper-Free Click Chemistry
  作者：Sara V. Orski、Andrei A. Poloukhtine、Selvanathan Arumugam、Leidong Mao、Vladimir V. Popik、Jason Locklin

  DOI：10.1021/ja105066t

  日期：2010.8.18

  Surfaces containing reactive ester polymer brushes were functionalized with cyclopropenone-masked dibenzocyclooctynes for the light activated immobilization of azides using catalyst-free click chemistry. The photodecarbonylation reaction in the amorphous brush layer is first order for the first 45 s with a rate constant of 0.022 s(-1). The catalyst-free cycloaddition of surface bound dibeznocyclooctynes proceeds rapidly in the presence of azides under ambient conditions. Photolithography using a shadow mask was used to demonstrate patterning with multiple azide containing molecules. This surface immobilization strategy provides a general and facile platform for the generation of multicomponent surfaces with spatially resolved chemical functionality.
• METHOD FOR IN VIVO TARGETING OF NANOPARTICLES VIA BIOORTHOGONAL COPPER-FREE CLICK CHEMISTRY
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20130251784A1

  公开（公告）日：2013-09-26

  The present disclosure relates to a method for in vivo targeting of a nanoparticle via bioorthogonal copper-free click chemistry, more particularly to a method for in vivo targeting of a nanoparticle, including: injecting a precursor capable of being metabolically engineered in vivo when injected into a living system and having a first bioorthogonal functional group into the living system; and injecting a nanoparticle having a second bioorthogonal functional group which can perform a bioorthogonal copper-free click reaction with the first bioorthogonal functional group attached thereto into the living system. In accordance with the present disclosure, accumulation of nanoparticles at a target site in a living system can be increased remarkably and the biodistribution of the nanoparticles can be controlled since the nanoparticles bound to a cell surface are taken up into the cell with time.