spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)] | 23022-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)]
• 英文别名: 1,3,3-Trimethylspiro；1',3',3'-trimethyl-1',3'-dihydro-spiro[chromene-2,2'-indol]-8-ol；1',3',3'-Trimethylspiro[chromene-2,2'-indole]-8-ol
• CAS: 23022-12-0
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: ISAUQFGDEYZXDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)] 、 6-溴己基丙-2-烯酸酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丁酮 为溶剂， 生成 6-(1',3',3'-Trimethylspiro[chromene-2,2'-indole]-8-yl)oxyhexyl prop-2-enoate
  参考文献：
  名称：

  Molecular Design of Light-Responsive Hydrogels, For in Situ Generation of Fast and Reversible Valves for Microfluidic Applications

  摘要：

  通过优化螺吡喃光开关的分子设计和凝胶成分，获得了具有与微流体兼容的响应特性的可逆光响应水凝胶阀。利用自质子化凝胶配方，在水凝胶网络中共聚丙烯酸作为内部质子供体，从而使水凝胶在 pH 值为中性的水中处于膨胀状态。通过共聚螺吡喃发色团，赋予水凝胶光响应特性，利用电子汲取基团和电子捐赠基团调节凝胶的膨胀和收缩行为。在所有情况下，收缩都是由水扩散速率决定的，而膨胀则是由异构化动力学决定的。在一种水凝胶中，观察到了可逆和可重复的体积变化。最后，还制造出了集成在微流体通道中的凝胶阀，可在几分钟内打开和关闭阀门，实现可逆和可重复的操作。

  DOI：

  10.1021/acs.chemmater.5b01860
• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 、 2,3-二羟基苯甲醛 以 neat (no solvent) 为溶剂， 反应 0.17h， 以99%的产率得到spiro[2H-1-benzopyran-2,2’-(8-hydroxy-1’,3’,3’-trimethylindoline)]
  参考文献：
  名称：

  Improving the Synthesis of Spiropyran Derivatives Using Microwave Irradiation Method

  摘要：

  A solvent free synthesis of spiropyran derivatives has been developed from the condensation of indoline and salicylaldehyde using a microwave irradiation method. This method starts from readily available starting materials and provides biologically interesting products. The microwave irradiation method was remarkably successful and gave spiropyran derivatives in higher yield (72-99%) with a much shorter reaction time (10-15 min) compared to the conventional heating method. The chemical structures of the compounds prepared were characterized through IR, H-1 NMR and C-13 NMR spectral data.

  DOI：

  10.3987/com-13-12920

文献信息

• US5551973A
  申请人：——

  公开号：US5551973A

  公开（公告）日：1996-09-03
• US5593486A
  申请人：——

  公开号：US5593486A

  公开（公告）日：1997-01-14
• US5633109A
  申请人：——

  公开号：US5633109A

  公开（公告）日：1997-05-27
• Improving the Synthesis of Spiropyran Derivatives Using Microwave Irradiation Method
  作者：Siti Aishah Hasbullah、Atisya Rohadi、Azwan Mat Lazim、Rumaisa Nordin

  DOI：10.3987/com-13-12920

  日期：——

  A solvent free synthesis of spiropyran derivatives has been developed from the condensation of indoline and salicylaldehyde using a microwave irradiation method. This method starts from readily available starting materials and provides biologically interesting products. The microwave irradiation method was remarkably successful and gave spiropyran derivatives in higher yield (72-99%) with a much shorter reaction time (10-15 min) compared to the conventional heating method. The chemical structures of the compounds prepared were characterized through IR, H-1 NMR and C-13 NMR spectral data.
• Molecular Design of Light-Responsive Hydrogels, For in Situ Generation of Fast and Reversible Valves for Microfluidic Applications
  作者：Jeroen ter Schiphorst、Simon Coleman、Jelle E. Stumpel、Aymen Ben Azouz、Dermot Diamond、Albertus P. H. J. Schenning

  DOI：10.1021/acs.chemmater.5b01860

  日期：2015.9.8

  Reversible light-responsive hydrogel valves with response characteristics compatible for microfluidics have been obtained by optimization of molecular design of spiropyran photoswitches and gel composition. Self-protonating gel formulations were exploited, wherein acrylic acid was copolymerized in the hydrogel network as an internal proton donor, to achieve a swollen state of the hydrogel in water at neutral pH. Light-responsive properties were endowed upon the hydrogels by copolymerization of spiropyran chromophores, using electron withdrawing and donating groups to tune the gel-swelling and shrinkage behavior. In all cases, the shrinkage was determined by the water diffusion rate, while for the swelling the isomerization kinetics is the rate-determining step. For one hydrogel, reversible and reproducible volume changes were observed. Finally, gel-valves integrated within microfluidic channels were fabricated, allowing reversible and repeatable operation, with opening and closing of the valve in minutes.

  通过优化螺吡喃光开关的分子设计和凝胶成分，获得了具有与微流体兼容的响应特性的可逆光响应水凝胶阀。利用自质子化凝胶配方，在水凝胶网络中共聚丙烯酸作为内部质子供体，从而使水凝胶在 pH 值为中性的水中处于膨胀状态。通过共聚螺吡喃发色团，赋予水凝胶光响应特性，利用电子汲取基团和电子捐赠基团调节凝胶的膨胀和收缩行为。在所有情况下，收缩都是由水扩散速率决定的，而膨胀则是由异构化动力学决定的。在一种水凝胶中，观察到了可逆和可重复的体积变化。最后，还制造出了集成在微流体通道中的凝胶阀，可在几分钟内打开和关闭阀门，实现可逆和可重复的操作。