2-nitro-5a-(4-phenylphenylene)-6,6-dimethyl-5a,6-dihydro-12H-indolo[2,1-b][1,3]benzooxazine | 1206829-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-nitro-5a-(4-phenylphenylene)-6,6-dimethyl-5a,6-dihydro-12H-indolo[2,1-b][1,3]benzooxazine
• 英文别名: 6,6-dimethyl-2-nitro-5a-(4-phenylphenyl)-12H-indolo[2,1-b][1,3]benzoxazine
• CAS: 1206829-67-5
• 化学式: C₂₉H₂₄N₂O₃
• 分子量: 448.521
• InChiKey: LGFFLNXHMXZSSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-1-(4-苯基苯基)丙烷-1-酮 在 溶剂黄146 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 生成 2-nitro-5a-(4-phenylphenylene)-6,6-dimethyl-5a,6-dihydro-12H-indolo[2,1-b][1,3]benzooxazine
  参考文献：
  名称：

  快速稳定的光致变色恶嗪用于荧光转换

  摘要：

  衍射对荧光显微镜的空间分辨率施加的严格限制要求确定可行的策略以在光学控制下切换荧光。在这种情况下，光致变色化合物的光诱导和可逆转变是特别有价值的。实际上，可以对这些分子进行改造以响应光学刺激来调节互补荧光团的发射强度。在此一般设计逻辑的基础上，我们组装了一个功能分子构建体，该构建体由硼二吡咯亚甲基荧光团和硝基螺吡喃荧光染料组成，并证明了前者的发射可以通过后者的相互转换进行调节。但是，这种荧光团-光致染料二色化合物的开关速度较慢，且抗疲劳性较差。为了改善这两个参数，我们基于恶嗪环的光致打开和热闭合，开发了一个新的光致变色开关系列。这些化合物在纳秒至微秒的时间尺度上在闭环和开环异构体之间来回切换，并且可以承受数千次切换循环而没有降解迹象。另外，可以利用适当的发色片段在其可切换的恶嗪环上的附着来响应于一对激发光束的照射而使荧光失活或可逆地失活。具体来说，我们组装了三个二联体，每个二联体均基于硼二

  DOI：

  10.1021/la201062h

文献信息

• Bichromophoric Photochromes Based on the Opening and Closing of a Single Oxazine Ring
  作者：Massimiliano Tomasulo、Salvatore Sortino、Françisco M. Raymo

  DOI：10.1021/jo7017119

  日期：2008.1.1

  photochromes based on the photoinduced opening and thermal closing of a [1,3]oxazine ring. In particular, we have synthesized six compounds incorporating fused 3H-indole and 4-nitrophenoxy fragments and pendant biphenyl, styryl, biphenylvinyl, or stilbenylvinyl groups. The laser excitation of two of these six molecules cleaves a [C−O] bond and opens their [1,3]oxazine ring in less than 6 ns with quantum yields

  我们基于[1,3]恶嗪环的光致开环和热闭环设计了双色性光致变色剂。特别是，我们已经合成了六种化合物，其中包含稠合的3 H-吲哚和4-硝基苯氧基片段以及侧链联苯，苯乙烯基，联苯乙烯基或二苯乙烯基乙烯基。这六个分子中的两个分子的激光激发使[C-O]键断裂，并在不到6 ns的时间内打开其[1,3]恶嗪环，其量子产率分别为0.08和0.28。该光诱导过程同时产生4-硝基苯酚酸根阴离子和3 H-吲哚阳离子。两个生色团在电磁光谱的相同区域吸收。结果，在ca处出现一个强带。在[1,3]恶嗪环的光诱导打开后的440 nm处。在这两种情况下，光生物质都分别以一级动力学和38 ns和140 ns的寿命切换回原始异构体。两种化合物均具有出色的抗疲劳性，并在刚性聚甲基丙烯酸甲酯基质中保留了其光化学性能。但是，聚合物基体内的热再异构化明显较慢，并且需要几微秒的时间才能发生。在其他相同的实验条件下，其他四种化合物在激
• Photochromic compounds based on ring opening and closing of an [1,3]oxazine compound
  申请人：Raymo Francisco M.

  公开号：US20110095243A1

  公开（公告）日：2011-04-28

  We have designed a molecular switch based on the photoinduced opening and thermal closing of a [1,3]oxazine ring. A substituted [1,3]oxazine compound described as having a general (i.e., unsubstituted) structure with fused indoline and benzooxazine fragments such that they share a common bond in the [1,3]oxazine compound: (i) the bond connecting positions 1 and 2 of the indoline fragment and (ii) the bond connecting positions 2 and 3 of the benzooxazine fragment. Irradiation by light of suitable wavelength and intensity of this photochromic compound induces cleavage of a [C—O] bond of the [1,3]oxazine ring to form a phenolate chromophore. The photogenerated (e.g., colored) isomer may revert thermally to the starting (e.g., colorless) oxazine. Alternatively, the switch may be between isomers of the compound that absorb at different wavelengths. Reversible coloration of silica or polymeric materials and switching optical signals may involve many cycles of interconversion between different colored states. A colorless/colored state may be maintained by constant irradiation or chemical trapping.

  我们设计了一种基于[1,3]噁唑环的光诱导开合和热闭合的分子开关。该取代[1,3]噁唑化合物的结构为一般（即未取代）的结构，具有融合的吲哚啉和苯噁唑片段，使它们在[1,3]噁唑化合物中共享一个共同的键：（i）连接吲哚啉片段的1和2位置的键和（ii）连接苯噁唑片段的2和3位置的键。通过适当波长和强度的光照射这种光致变色化合物，可以引发[1,3]噁唑环的[C-O]键裂解，形成酚酸色团。光诱导的（例如有色的）异构体可以通过热反转回起始（例如无色的）噁唑。或者，开关可以在吸收不同波长的化合物异构体之间进行。可逆地染色硅胶或聚合材料和切换光学信号可能涉及多个不同着色状态之间的多个循环的相互转化。无色/有色状态可以通过恒定的照射或化学捕获来维持。
• Photochromic compounds based on ring opening and closing of an {1,3}oxazine compound
  申请人：Raymo M. Francisco

  公开号：US20070221889A1

  公开（公告）日：2007-09-27

  We have designed a molecular switch based on the photoinduced opening and thermal closing of a [1,3]oxazine ring. A substituted [1,3]oxazine compound described as having a general (i.e., unsubstituted) structure with fused indoline and benzooxazine fragments such that they share a common bond in the [1,3]oxazine compound: (i) the bond connecting positions 1 and 2 of the indoline fragment and (ii) the bond connecting positions 2 and 3 of the benzooxazine fragment. Irradiation by light of suitable wave-length and intensity of this photochromic compound induces cleavage of a [C—O] bond of the [1,3]oxazine ring to form a phenolate chromophore. The photogenerated (e.g., colored) isomer may revert thermally to the starting (e.g., colorless) oxazine. Alternatively, the switch may be between isomers of the compound that absorb at different wavelengths. Reversible coloration of silica or polymeric materials and switching optical signals may involve many cycles of interconversion between different colored states. A colorless/colored state may be maintained by constant irradiation or chemical trapping.
• US7790068B2
  申请人：——

  公开号：US7790068B2

  公开（公告）日：2010-09-07
• US8252209B2
  申请人：——

  公开号：US8252209B2

  公开（公告）日：2012-08-28