8-bromo-5a,6-dihydro-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine | 392669-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 8-bromo-5a,6-dihydro-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine
• 英文别名: 8-bromoindolo[2,1-b][1,3]benzoxazine；8-bromo-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine
• CAS: 392669-07-7
• 化学式: C₁₈H₁₇BrN₂O₃
• 分子量: 389.249
• InChiKey: CYANKAZOJWWUIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-5a,6-dihydro-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到8-(4-methoxyphenyl)-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine
  参考文献：
  名称：

  Improving the photochromic properties of indolo[2,1-b][1,3]benzoxazines with phenylic substituents

  摘要：

  This work presents a series of new photochromic compounds of indolo[2,1-b][1,3]benzoxazine family. Photochromic systems based on the opening and closing of [1,3]oxazine ring are among the fastest photochromic switches, completing the full "on-off" cycle in less than few tens of nanoseconds. Furthermore, indolo[2,1-b][1,3]benzoxazines are distinguished for their excellent fatigue resistance as well as substantial quantum yield of photochromic transformation, both important for practical applications. Photochromic properties can be selectively altered by introducing structural modifications to the parent compound, namely, by varying substituents attached to certain positions. We aimed to enhance the photochromic performance of indolo[2,1-b1[1,31benzoxazines by modifying the parent molecule with phenylic substituents. In this article we introduce 10 new compounds, which are classified into two groups according to the attachment site of the phenylic substituent: group I compounds have modifications in the 5th position of the indole ring, group II-in the 4th position of the indolo[2,1-b][1,3]benzoxazine molecule. The investigation of photochromic properties of the compounds in acetonitrile solutions revealed the outstanding parameters of the new molecules. Group I compounds have an exceptional feature in the induced absorption spectra - an additional band in the nIR, which is observed for the first time in the compounds of indolo[2,1-b][1,3]benzoxazine family. On the other hand, all group II compounds display enhanced switching speeds; indeed, the fastest relaxation time value ever reported for similar compounds was measured in this group. In general, group I compounds were found to be superior to both parent molecule and group II compounds in both photostability and quantum yield, thus demonstrating the potential of molecular design for development and realization of photochromic compounds with desired properties. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.12.022
• 作为产物：
  描述：

  2,3,3-三甲基-5-溴-3H-吲哚 、 2-氯甲基-4-硝基苯酚 以 硝基甲烷 为溶剂， 反应 24.0h， 以55%的产率得到8-bromo-5a,6-dihydro-5a,6,6-trimethyl-2-nitro-12H-indolo[2,1-b][1,3]benzoxazine
  参考文献：
  名称：

  Amankaviciene, Virgine; Asadauskas, Svajus J.; Girniene, Jolanta, Journal of Chemical Research, 2005, # 9, p. 580 - 582

  摘要：

  DOI：

文献信息

• Amankaviciene, Virgine; Asadauskas, Svajus J.; Girniene, Jolanta, Journal of Chemical Research, 2005, # 9, p. 580 - 582
  作者：Amankaviciene, Virgine、Asadauskas, Svajus J.、Girniene, Jolanta、Sackus, Algirdas

  DOI：——

  日期：——
• Improving the photochromic properties of indolo[2,1-b][1,3]benzoxazines with phenylic substituents
  作者：Vladislava Voiciuk、Kipras Redeckas、Vytas Martynaitis、Rasa Steponavičiūtė、Algirdas Šačkus、Mikas Vengris

  DOI：10.1016/j.jphotochem.2013.12.022

  日期：2014.3

  This work presents a series of new photochromic compounds of indolo[2,1-b][1,3]benzoxazine family. Photochromic systems based on the opening and closing of [1,3]oxazine ring are among the fastest photochromic switches, completing the full "on-off" cycle in less than few tens of nanoseconds. Furthermore, indolo[2,1-b][1,3]benzoxazines are distinguished for their excellent fatigue resistance as well as substantial quantum yield of photochromic transformation, both important for practical applications. Photochromic properties can be selectively altered by introducing structural modifications to the parent compound, namely, by varying substituents attached to certain positions. We aimed to enhance the photochromic performance of indolo[2,1-b1[1,31benzoxazines by modifying the parent molecule with phenylic substituents. In this article we introduce 10 new compounds, which are classified into two groups according to the attachment site of the phenylic substituent: group I compounds have modifications in the 5th position of the indole ring, group II-in the 4th position of the indolo[2,1-b][1,3]benzoxazine molecule. The investigation of photochromic properties of the compounds in acetonitrile solutions revealed the outstanding parameters of the new molecules. Group I compounds have an exceptional feature in the induced absorption spectra - an additional band in the nIR, which is observed for the first time in the compounds of indolo[2,1-b][1,3]benzoxazine family. On the other hand, all group II compounds display enhanced switching speeds; indeed, the fastest relaxation time value ever reported for similar compounds was measured in this group. In general, group I compounds were found to be superior to both parent molecule and group II compounds in both photostability and quantum yield, thus demonstrating the potential of molecular design for development and realization of photochromic compounds with desired properties. (C) 2014 Elsevier B.V. All rights reserved.