2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid | 1314022-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid
• 英文别名: 2-(4-Methoxyphenyl)-4h-thieno-[3,2-b]-pyrrole-5-carboxylic acid
• CAS: 1314022-94-0
• 化学式: C₁₄H₁₁NO₃S
• 分子量: 273.312
• InChiKey: YLUJKUBKWYRUEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid 在 铜 作用下， 以 喹啉 为溶剂， 反应 3.0h， 以164 mg的产率得到2-(4-methoxy-phenyl)-4H-thieno[3,2-b]pyrrole
  参考文献：
  名称：

  BODIPY Derivatives and Methods of Synthesis and Use Thereof

  摘要：

  BODIPY（硼二吡咯甲烷二氟化物）衍生物及其合成和用途被披露。

  公开号：

  US20150158888A1
• 作为产物：
  描述：

  5-(4-甲氧基苯基)噻酚-2-甲醛 在 sodium ethanolate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.33h， 生成 2-(4-methoxyphenyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid
  参考文献：
  名称：

  Singlet Oxygen Generation by Novel NIR BODIPY Dyes

  摘要：

  Five novel near-infrared BODIPY dyes were prepared for improved singlet oxygen generation using thiophene and bromine. Theoretical, optical, photostable, and singlet oxygen generation characteristics of these dyes were assessed. Predicted excitation energies by TDDFT calculations were in good agreement (Delta E approximate to 0.06 eV) with experimental data. All five dyes showed both excitation and emission In the NIR range. In particular, two dyes having sulfur and bromine atoms showed efficient singlet oxygen generation with high photostability.

  DOI：

  10.1021/ol2014076

文献信息

• PEG conjugated BODIPY-Br₂ as macro-photosensitizer for efficient imaging-guided photodynamic therapy
  作者：Zheng Ruan、Yangyang Zhao、Pan Yuan、Le Liu、Yucai Wang、Lifeng Yan

  DOI：10.1039/c7tb02924a

  日期：——

  Drug-free biocompatible nanoparticles with photosensitizers as both diagnostic and therapy agents represent an emerging approach for imaging-guided photodynamic therapy (PDT). Here, a NSH-active boron-dipyrromethene (BODIPY) derivative with a bromine substituted (BODIPY-Br2, for simplicity, BDP-Br) photosensitizer was synthesized; it showed a high ability of generating reactive oxygen species (ROS)

  具有光敏剂作为诊断剂和治疗剂的无药物生物相容性纳米颗粒代表了成像引导的光动力疗法（PDT）的新兴方法。在此，合成了具有溴取代的（BODIPY-Br 2，为简化起见，BDP-Br）光敏剂的NSH活性硼二吡咯亚甲基（BODIPY）衍生物；它显示了在PDT照射下具有很高的产生活性氧（ROS）的能力和近红外荧光成像能力。然后，制备了一种简单的聚乙二醇化的BDP-Br（PEG-BDP）作为一种大型光敏剂，它在体外和体内均表现出优异的细胞摄取能力，高成像效率以及PDT治疗的效果。。用4T1原位肿瘤模型给药后，与游离BDP-Br分子相比，所得PEG-BDP表现出延长的血液循环和优先的肿瘤蓄积。一旦在肿瘤组织中积累，PEG-BDP的治疗效果就可以显着抑制原发性肿瘤的生长，并且在低至35 mW cm -2的弱辐射能量下持续20分钟没有明显的副作用。这种简单结构的宏观光敏剂的名称为有效的成像指导的癌症PDT提供了新途径。
• Thiophene-fused boron dipyrromethenes as energy efficient near-infrared photocatalysts for radical polymerizations
  作者：Alex Stafford、Seth R. Allen、Tod A. Grusenmeyer、Connor J. O'Dea、Laura Estergreen、Sean T. Roberts、Zachariah A. Page

  DOI：10.1039/d3ta04462a

  日期：——

  A series of thiophene-fused boron dipyrromethene (BODIPY) photoredox catalysts are systematically examined to identify structure–reactivity relationships that enable efficient near-infrared light-induced polymerizations.

  我们系统地研究了一系列噻吩熔融二吡咯烷硼（BODIPY）光氧化催化剂，以确定能够实现高效近红外光诱导聚合的结构-反应关系。
• US9611281B2
  申请人：——

  公开号：US9611281B2

  公开（公告）日：2017-04-04
• BODIPY Derivatives and Methods of Synthesis and Use Thereof
  申请人：The Board of Regents of the University of Oklahoma

  公开号：US20150158888A1

  公开（公告）日：2015-06-11

  Derivatives of BODIPY (boron dipyrromethene difluoride) and their synthesis and use are disclosed.

  BODIPY（硼二吡咯甲烷二氟化物）衍生物及其合成和用途被披露。
• Singlet Oxygen Generation by Novel NIR BODIPY Dyes
  作者：Samuel G. Awuah、Jason Polreis、Vidya Biradar、Youngjae You

  DOI：10.1021/ol2014076

  日期：2011.8.5

  Five novel near-infrared BODIPY dyes were prepared for improved singlet oxygen generation using thiophene and bromine. Theoretical, optical, photostable, and singlet oxygen generation characteristics of these dyes were assessed. Predicted excitation energies by TDDFT calculations were in good agreement (Delta E approximate to 0.06 eV) with experimental data. All five dyes showed both excitation and emission In the NIR range. In particular, two dyes having sulfur and bromine atoms showed efficient singlet oxygen generation with high photostability.