3-bromo-2-methyl-5-(3-methylphenyl)thiophene | 898554-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-bromo-2-methyl-5-(3-methylphenyl)thiophene
• CAS: 898554-52-4
• 化学式: C₁₂H₁₁BrS
• 分子量: 267.189
• InChiKey: ZCPHAHCBBXUYML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-2-methyl-5-(3-methylphenyl)thiophene 、 (2-methyl-1-naphthyl)perfluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以42%的产率得到1-(2-methyl-1-naphthyl)-2-[2-methyl-5-(3-methylphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Photochromic diarylethenes with a naphthalene moiety: synthesis, photochromism, and substitution effects

  摘要：

  Five unsymmetrical diarylethenes with a naphthalene moiety were synthesized, and the structures of four diarylethenes were determined by single crystal X-ray diffraction analysis. The naphthalene was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. Their properties, such as photochromism, thermal stability, fatigue resistance, and fluorescence, were investigated systematically. All five diarylethenes, which are thermally stable, exhibit favorable photochromism, and function as notable fluorescence switches in both solution and solid media. The electron-donating substituents effectively suppressed the cycloreversion quantum yield, whereas the electron-withdrawing substituents evidently enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. The results indicated that the naphthalene moiety and the substituent effects played an important role during the process of photoisomerization reaction for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.080
• 作为产物：
  描述：

  3,5-二溴-2-甲基噻吩 在 四(三苯基膦)钯 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 16.5h， 生成 3-bromo-2-methyl-5-(3-methylphenyl)thiophene
  参考文献：
  名称：

  Synthesis, crystal structure and its optical and electrochemical properties of a new unsymmetrical diarylethene

  摘要：

  A new unsymmetrical photochromic diarylethene, 1- (2-methyl-5-phenyl-3-thienyl),2-(2-methyl-5-(3-methylphenyl)-3-thienyl)3,3,4,4,5,5-hexafluorocyclopent-l-ene (MPMTH), was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. Its optical and electrochemical properties, including photochromic reactivity both in solution and in the crystalline phase, fluorescence and electrochemical property were investigated. The diarylethene underwent reversible photochromism, changing from colorless to blue after irradiation with UV light or visible light. The maximum absorption of the closed-ring isomer of MPMTH was observed at 577 nm in hexane. In hexane, the open-ring isomer of MPMTH exhibited relatively strong fluorescence at 310 nm when excited at 280 nm. The irreversible anodic oxidation of MPMTH was observed by performing linear sweep experiment. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.08.027

文献信息

• HETEROCYCLIC DERIVATIVE AND USE THEREOF
  申请人：Matsunaga Nobuyuki

  公开号：US20110028493A1

  公开（公告）日：2011-02-03

  The present invention aims to provide a compound having superior pharmacological action, physicochemical properties and the like and useful as an sGC activation drug, or an agent for the prophylaxis and/or treatment of diseases such as hypertension, ischemic cardiac disease, cardiac failure, kidney disease, arteriosclerotic disease, atrial fibrillation, pulmonary hypertension, diabetes, diabetic complications, metabolic syndrome, peripheral arterial obstruction, erectile dysfunction and the like. An sGC activation drug containing a compound represented by the formula (II): wherein each symbol is as defined in the specification, or a salt thereof, as an active ingredient.

  本发明旨在提供一种具有优异的药理作用、物理化学性质等，并且可用作sGC激活药物、高血压、缺血性心脏病、心力衰竭、肾脏疾病、动脉硬化疾病、心房颤动、肺动脉高压、糖尿病、糖尿病并发症、代谢综合征、周围动脉阻塞、勃起功能障碍等疾病的预防和/或治疗剂的化合物。其中，所述化合物为式（II）所表示的化合物或其盐，作为活性成分的sGC激活药物。式（II）中，各符号如规范中定义的。
• US8461348B2
  申请人：——

  公开号：US8461348B2

  公开（公告）日：2013-06-11
• Synthesis, crystal structure and its optical and electrochemical properties of a new unsymmetrical diarylethene
  作者：Shouzhi Pu、Gang Liu、Guizhen Li、Ruji Wang、Tianshe Yang

  DOI：10.1016/j.molstruc.2006.08.027

  日期：2007.5

  A new unsymmetrical photochromic diarylethene, 1- (2-methyl-5-phenyl-3-thienyl),2-(2-methyl-5-(3-methylphenyl)-3-thienyl)3,3,4,4,5,5-hexafluorocyclopent-l-ene (MPMTH), was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. Its optical and electrochemical properties, including photochromic reactivity both in solution and in the crystalline phase, fluorescence and electrochemical property were investigated. The diarylethene underwent reversible photochromism, changing from colorless to blue after irradiation with UV light or visible light. The maximum absorption of the closed-ring isomer of MPMTH was observed at 577 nm in hexane. In hexane, the open-ring isomer of MPMTH exhibited relatively strong fluorescence at 310 nm when excited at 280 nm. The irreversible anodic oxidation of MPMTH was observed by performing linear sweep experiment. (C) 2006 Elsevier B.V. All rights reserved.
• Photochromic diarylethenes with a naphthalene moiety: synthesis, photochromism, and substitution effects
  作者：Renjie Wang、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.tet.2013.04.080

  日期：2013.7

  Five unsymmetrical diarylethenes with a naphthalene moiety were synthesized, and the structures of four diarylethenes were determined by single crystal X-ray diffraction analysis. The naphthalene was connected directly to the central perfluorocyclopentene ring as an aryl moiety and available to participate in photoisomerization reaction. Their properties, such as photochromism, thermal stability, fatigue resistance, and fluorescence, were investigated systematically. All five diarylethenes, which are thermally stable, exhibit favorable photochromism, and function as notable fluorescence switches in both solution and solid media. The electron-donating substituents effectively suppressed the cycloreversion quantum yield, whereas the electron-withdrawing substituents evidently enhanced the fluorescence quantum yield of diarylethenes with a naphthalene moiety. The results indicated that the naphthalene moiety and the substituent effects played an important role during the process of photoisomerization reaction for these diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.