1-(4-(allyloxy)-3,5-dichlorophenyl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(allyloxy)-3,5-dichlorophenyl)ethan-1-one
• 英文别名: 1-(3,5-Dichloro-4-prop-2-enoxyphenyl)ethanone
• 化学式: C₁₁H₁₀Cl₂O₂
• 分子量: 245.105
• InChiKey: BIFGJUYUTQSAJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(allyloxy)-3,5-dichlorophenyl)ethan-1-one 在 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 51.0h， 生成 1-(4-(allyloxy)-3,5-dichlorophenyl)-3-(4-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)phenyl)-4-nitrobutan-1-one
  参考文献：
  名称：

  Photoacoustic Probes for Ratiometric Imaging of Copper(II)

  摘要：

  Photoacoustic tomography has emerged as a promising alternative to MRI and X-ray scans in the clinical setting due to its ability to afford high-resolution images at depths in the cm range. However, its utility has not been established in the basic research arena owing to a lack of analyte-specific photoacoustic probes. To this end, we have developed acoustogenic probes for copper(II)-1 and, -2 (APC-1 and APC-2, a water-soluble congener) for the chemoselective visualization of Cu(II), a metal ion which plays a crucial role in chronic neurological disorders such as Alzheimer's disease. To detect Cu(II), we have equipped both APCs with a 2-picolinic ester sensing module that is readily hydrolyzed in the presence of Cu(II) but not :by other divalent metal ions. Additionally, we designed APC-1 and APC-2 explicitly for ratiometric photoacoustic imaging by using an aza-BODIPY dye scaffold exhibiting two spectrally resolved NIR absorbance bands which correspond to the 2-picolinic ester capped and uncapped phenoxide forms. The normalized ratiometric turn-on responses for APC-1 and APC-2 were 89- and: 101-fold, respectively.

  DOI：

  10.1021/jacs.5b10504
• 作为产物：
  描述：

  2,6-二氯苯酚 在 三乙胺 作用下， 以 二氯甲烷 、 三氟甲磺酸 为溶剂， 反应 4.0h， 生成 1-(4-(allyloxy)-3,5-dichlorophenyl)ethan-1-one
  参考文献：
  名称：

  促进细胞摄取和增强肿瘤寻求染料的光声特性的仿生方法

  摘要：

  葡萄糖与药物和显像剂的结合能够通过与细胞表面过度表达的 GLUT1 的相互作用实现癌细胞靶向。虽然这种修饰的另一个好处是碳水化合物的增溶作用，但在成像剂的情况下，水溶性并不能保证减少 π 堆积或聚集。由此产生的吸收光谱变宽不利于光声 (PA) 成像，因为信号强度、精度和图像质量都依赖于可靠的光谱分离。为了解决这一主要限制并进一步增强显像剂的肿瘤靶向能力，我们采用仿生方法设计多价葡萄糖部分 (mvGlu)。我们通过开发基于 aza-BODIPY 的造影剂展示了这一新组的效用，该造影剂在光谱解混合后具有超过 11 倍的显着 PA 信号增强。此外，当应用于靶向癌细胞时，可以使用超低染料浓度 (50 nM) 实现有效染色，并且与非靶向类似物相比，信号强度高 > 1000 倍。最后，我们采用 mvGlu 技术开发了一种逻辑门控声源探针，用于检测乳腺癌小鼠模型中肿瘤内铜（即 Cu(I)），这是一种新兴

  DOI：

  10.1021/jacs.2c13489

文献信息

• A Conformationally Restricted Aza-BODIPY Platform for Stimulus-Responsive Probes with Enhanced Photoacoustic Properties
  作者：Effie Y. Zhou、Hailey J. Knox、Chang Liu、Weili Zhao、Jefferson Chan

  DOI：10.1021/jacs.9b06694

  日期：2019.11.6

  rational manner. Herein we synthesized and evaluated six modifications to the aza-BODIPY dye platform with respect to their absorbance, fluorescence, and PA properties. We identified a promising conformationally restricted aza-BODIPY (CRaB) scaffold that prioritizes three criteria necessary for the design of stimulus-responsive dyes with optimal ratiometric PA response: absorbance at NIR wavelengths, strong

  光声 (PA) 染料吸收近红外 (NIR) 光以产生超声波信号，可以在厘米深度的组织中检测到，其分辨率明显高于使用基于荧光的方法成像的染料。因此，PA 试剂作为研究活体动物疾病模型的研究工具显示出巨大的前景。然而，可激活的 PA 探针的开发受到了适当的 PA 活性分子平台的相对稀缺性的阻碍，这些平台具有可以以合理方式操纵的特性。在此，我们合成并评估了 aza-BODIPY 染料平台在吸光度、荧光和 PA 特性方面的六种修改。我们确定了一种有前途的构象限制 aza-BODIPY (CRaB) 支架，它优先考虑了设计具有最佳比例 PA 响应的刺激响应染料所需的三个标准：NIR 波长处的吸光度、强 PA 强度和与所需刺激相互作用时的大 Δλ . 使用这种支架，我们合成了三种化学上不同的刺激响应 PA 探针，并证明了体外理论比率响应的 2 到 8 倍改进。这表明 PA 参数的改进是可推广的。最后，我们验证了每个
• A general strategy to optimize the performance of aza-BODIPY-based probes for enhanced photoacoustic properties
  作者：Anuj K. Yadav、Rodrigo Tapia Hernandez、Jefferson Chan

  DOI：10.1016/bs.mie.2021.06.022

  日期：——
• Photoacoustic Probes for Ratiometric Imaging of Copper(II)
  作者：Hao Li、Pamela Zhang、Lukas P. Smaga、Ryan A. Hoffman、Jefferson Chan

  DOI：10.1021/jacs.5b10504

  日期：2015.12.23

  Photoacoustic tomography has emerged as a promising alternative to MRI and X-ray scans in the clinical setting due to its ability to afford high-resolution images at depths in the cm range. However, its utility has not been established in the basic research arena owing to a lack of analyte-specific photoacoustic probes. To this end, we have developed acoustogenic probes for copper(II)-1 and, -2 (APC-1 and APC-2, a water-soluble congener) for the chemoselective visualization of Cu(II), a metal ion which plays a crucial role in chronic neurological disorders such as Alzheimer's disease. To detect Cu(II), we have equipped both APCs with a 2-picolinic ester sensing module that is readily hydrolyzed in the presence of Cu(II) but not :by other divalent metal ions. Additionally, we designed APC-1 and APC-2 explicitly for ratiometric photoacoustic imaging by using an aza-BODIPY dye scaffold exhibiting two spectrally resolved NIR absorbance bands which correspond to the 2-picolinic ester capped and uncapped phenoxide forms. The normalized ratiometric turn-on responses for APC-1 and APC-2 were 89- and: 101-fold, respectively.
• Biomimetic Approach to Promote Cellular Uptake and Enhance Photoacoustic Properties of Tumor-Seeking Dyes
  作者：Amanda K. East、Michael C. Lee、Chang Jiang、Qasim Sikander、Jefferson Chan

  DOI：10.1021/jacs.2c13489

  日期：——

  The resulting broadening of the absorbance spectrum is a detriment to photoacoustic (PA) imaging since the signal intensity, accuracy, and image quality all rely on reliable spectral unmixing. To address this major limitation and further enhance the tumor-targeting ability of imaging agents, we have taken a biomimetic approach to design a multivalent glucose moiety (mvGlu). We showcase the utility

  葡萄糖与药物和显像剂的结合能够通过与细胞表面过度表达的 GLUT1 的相互作用实现癌细胞靶向。虽然这种修饰的另一个好处是碳水化合物的增溶作用，但在成像剂的情况下，水溶性并不能保证减少 π 堆积或聚集。由此产生的吸收光谱变宽不利于光声 (PA) 成像，因为信号强度、精度和图像质量都依赖于可靠的光谱分离。为了解决这一主要限制并进一步增强显像剂的肿瘤靶向能力，我们采用仿生方法设计多价葡萄糖部分 (mvGlu)。我们通过开发基于 aza-BODIPY 的造影剂展示了这一新组的效用，该造影剂在光谱解混合后具有超过 11 倍的显着 PA 信号增强。此外，当应用于靶向癌细胞时，可以使用超低染料浓度 (50 nM) 实现有效染色，并且与非靶向类似物相比，信号强度高 > 1000 倍。最后，我们采用 mvGlu 技术开发了一种逻辑门控声源探针，用于检测乳腺癌小鼠模型中肿瘤内铜（即 Cu(I)），这是一种新兴