trans-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol | 109976-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: trans-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol
• 英文别名: 2-hydroxy-3,5,6-trichloro-4'-methylazobenzene
• CAS: 109976-80-9
• 化学式: C₁₃H₉Cl₃N₂O
• 分子量: 315.586
• InChiKey: WVJUGALGASLMKC-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol 以 乙腈 为溶剂， 生成 cis-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol
  参考文献：
  名称：

  2-羟基偶氮苯通过光调节pH脉冲和振荡

  摘要：

  本文评估了2-羟基偶氮苯平台，该平台用于调整质子浓度脉冲和单色光的振荡。易于制备的2-羟基偶氮苯在近紫外线范围内表现出较大的吸收率。通过UV / Vis吸收，1 H NMR光谱和稳态荧光发射研究了光致异构化。在整个研究的系列中，2-羟基偶氮苯基序的反式立体异构体提供相应的顺式衍生物，其作用截面在10 3  M -1  cm -1范围内。同时，光异构化伴随着显着的p K苯酚基团的下降。根据苯基取代基图案，顺式-到-反式热回异构化可以在10毫秒-100秒范围内调谐。通过适当地调整2-羟基偶氮苯溶液的单波长照射，在10 s的时间尺度上可获得多达2个单位的可逆pH下降或pH振荡。

  DOI：

  10.1002/chem.201000541
• 作为产物：
  描述：

  cis-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol 以 乙腈 为溶剂， 生成 trans-3,4,6-trichloro-2-(4-methyl-phenylazo)-phenol
  参考文献：
  名称：

  2-羟基偶氮苯通过光调节pH脉冲和振荡

  摘要：

  本文评估了2-羟基偶氮苯平台，该平台用于调整质子浓度脉冲和单色光的振荡。易于制备的2-羟基偶氮苯在近紫外线范围内表现出较大的吸收率。通过UV / Vis吸收，1 H NMR光谱和稳态荧光发射研究了光致异构化。在整个研究的系列中，2-羟基偶氮苯基序的反式立体异构体提供相应的顺式衍生物，其作用截面在10 3  M -1  cm -1范围内。同时，光异构化伴随着显着的p K苯酚基团的下降。根据苯基取代基图案，顺式-到-反式热回异构化可以在10毫秒-100秒范围内调谐。通过适当地调整2-羟基偶氮苯溶液的单波长照射，在10 s的时间尺度上可获得多达2个单位的可逆pH下降或pH振荡。

  DOI：

  10.1002/chem.201000541

文献信息

• PHOTORESPONSIVE SUNSCREEN COMPOSITION
  申请人：Blueshift Pharma GmbH

  公开号：EP2467122A2

  公开（公告）日：2012-06-27
• Photoresponsive Sunscreen Composition
  申请人：Walzel Bernd

  公开号：US20120148647A1

  公开（公告）日：2012-06-14

  The present invention relates to a composition containing a sunscreen agent capable of undergoing protonation or deprotonation to form a protonated or deprotonated, respectively, sunscreen agent which absorbs, scatters or reflects more or less UV radiation than it does before being protonated or deprotonated, respectively, and a photoresponsive acid or base generating system which is capable of protonating or deprotonating, respectively, said sunscreen agent when the composition is exposed to UV radiation. Further subject matter of the present invention is a microcapsule comprising a sunscreen agent capable of undergoing protonation or deprotonation to form a protonated or deprotonated, respectively, sunscreen agent which absorbs, scatters or reflects more or less UV radiation than said sunscreen agent does before being protonated or deprotonated, respectively, wherein said sunscreen agent is present in said microcapsule substantially in its protonated or deprotonated form that absorbs, scatters or reflects less UV radiation than said sunscreen agent does upon protonation or deprotonation, respectively. The composition and microcapsule according to the invention are particularly useful for providing sunscreen formulations for cosmetic applications and for providing dermatological formulations for medical applications.
• [EN] PHOTORESPONSIVE SUNSCREEN COMPOSITION<br/>[FR] COMPOSITION D'ÉCRAN SOLAIRE PHOTOSENSIBLE
  申请人：BLUESHIFT PHARMA GMBH

  公开号：WO2011020928A2

  公开（公告）日：2011-02-24

  The present invention relates to a composition containing a sunscreen agent capable of undergoing protonation or deprotonation to form a protonated or deprotonated, respectively, sunscreen agent which absorbs, scatters or reflects more or less UV radiation than it does before being protonated or deprotonated, respectively, and a photoresponsive acid or base generating system which is capable of protonating or deprotonating, respectively, said sunscreen agent when the composition is exposed to UV radiation. Further subject matter of the present invention is a microcapsule comprising a sunscreen agent capable of undergoing protonation or deprotonation to form a protonated or deprotonated, respectively, sunscreen agent which absorbs, scatters or reflects more or less UV radiation than said sunscreen agent does before being protonated or deprotonated, respectively, wherein said sunscreen agent is present in said microcapsule substantially in its protonated or deprotonated form that absorbs, scatters or reflects less UV radiation than said sunscreen agent does upon protonation or deprotonation, respectively. The composition and microcapsule according to the invention are particularly useful for providing sunscreen formulations for cosmetic applications and for providing dermatological formulations for medical applications.
• 2-Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light
  作者：Matthieu Emond、Thomas Le Saux、Sylvie Maurin、Jean-Bernard Baudin、Raphael Plasson、Ludovic Jullien

  DOI：10.1002/chem.201000541

  日期：2010.8.2

  evaluates the 2‐hydroxyazobenzene platform for tailoring proton concentration pulses and oscillations with monochromatic light. The easily prepared 2‐hydroxyazobenzenes exhibit large absorptions in the near‐UV range. Photoisomerization was investigated by UV/Vis absorption, 1H NMR spectroscopy, and steady‐state fluorescence emission. In the whole investigated series, the trans stereoisomer of the 2‐hydroxyazobenzene

  本文评估了2-羟基偶氮苯平台，该平台用于调整质子浓度脉冲和单色光的振荡。易于制备的2-羟基偶氮苯在近紫外线范围内表现出较大的吸收率。通过UV / Vis吸收，1 H NMR光谱和稳态荧光发射研究了光致异构化。在整个研究的系列中，2-羟基偶氮苯基序的反式立体异构体提供相应的顺式衍生物，其作用截面在10 3  M -1  cm -1范围内。同时，光异构化伴随着显着的p K苯酚基团的下降。根据苯基取代基图案，顺式-到-反式热回异构化可以在10毫秒-100秒范围内调谐。通过适当地调整2-羟基偶氮苯溶液的单波长照射，在10 s的时间尺度上可获得多达2个单位的可逆pH下降或pH振荡。