(5-methyl-2-phenylthiazol-4-yl)boronic acid | 1313913-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5-methyl-2-phenylthiazol-4-yl)boronic acid
• 英文别名: 5-methyl-2-phenylthiazole-4-boronic acid；2-methyl-5-phenylthiazol-3-ylboronic acid；(2-phenyl-5-methyl-4-thiazolyl)boronic acid；2-phenyl-5-methylthiazole-4-boronic acid；(2-phenyl-5-methylthiazol-4-yl)boronic acid；(5-Methyl-2-phenyl-1,3-thiazol-4-yl)boronic acid；(5-methyl-2-phenyl-1,3-thiazol-4-yl)boronic acid
• CAS: 1313913-16-4
• 化学式: C₁₀H₁₀BNO₂S
• 分子量: 219.072
• InChiKey: LOUGWSZAZFPZOE-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-methyl-2-phenylthiazol-4-yl)boronic acid 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives

  摘要：

  2,3-Bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone 1-O, its monoethylene acetal 2-O and methylated derivatives 3-O and 4-O were synthesized and their photochromic properties were investigated. While bisarylnaphthoquinone 1-O was nonphotochromic, its monoacetal 2-O and methylated derivatives 3-O and 4-O displayed good photochromism. Among them, the isomer 4-O recorded a remarkable diastereomeric excess (98.40%) with high conversion ratio (96.20%) upon UV irradiation. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.01.016
• 作为产物：
  描述：

  2-苯基噻唑 在 正丁基锂 、 溴 、 methyloxirane 作用下， 以 四氢呋喃 为溶剂， 生成 (5-methyl-2-phenylthiazol-4-yl)boronic acid
  参考文献：
  名称：

  Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives

  摘要：

  2,3-Bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone 1-O, its monoethylene acetal 2-O and methylated derivatives 3-O and 4-O were synthesized and their photochromic properties were investigated. While bisarylnaphthoquinone 1-O was nonphotochromic, its monoacetal 2-O and methylated derivatives 3-O and 4-O displayed good photochromism. Among them, the isomer 4-O recorded a remarkable diastereomeric excess (98.40%) with high conversion ratio (96.20%) upon UV irradiation. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.01.016

文献信息

• The synthesis of new 3,4-(bisaryl)-1,8-naphthalimide and 2,3-(bisaryl)-7 H -benzimidazo[2,1-a]benzo[d]isoquinolin-7-one compounds and an investigation of their photochromic properties
  作者：Ersin ORHAN、Mahmut KÖSE、Tolga YAZAN

  DOI：10.3906/kim-1711-3

  日期：——

  Three new photochromic compounds, 3-(2,5-dimethyl-3-thienyl)-4-(2-phenyl-5-methyl-4-thiazolyl)-1,8-napht- halimide (1-O), 2,3-bis(2-phenyl-5-methyl-4-thiazolyl)-7$H$-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one (2-O), and 2,5-dimethyl-3-thienyl)-7$H$-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one (3-O), were synthesized and their photochromic properties were studied. Compound 1-O was synthesized by two consecutive Suzuki coupling reactions using 2,5-dimethylthiophene-3-boronic acid and 5-methyl-2-phenylthiazole-4-boronic acid. Photochromic compounds 2-O and 3-O were prepared by multistep reactions starting with 3-iodo-4-bromo-1,8-naphthalic anhydride and 2,5-dimethylthiophene-3-boronic acid or 2-phenyl-5-methylthiazole-4-boronic acid. All photochromic compounds showed a color change from colorless (or light yellow) to blue-green, purple, or orange colors (depending on the nature of the structures) on exposure to UV light at 365 nm in ethyl acetate solutions. The colored solutions can be reversed to the original colorless (or light yellow) solution by exposure to visible light at 530 nm.

  三种新的光致变色化合物：3-(2,5-二甲基-3-噻吩基)-4-(2-苯基-5-甲基-4-噻唑基)-1,8-萘卤酰亚胺（1-O）、2,3-双(2-苯基-5-甲基-4-噻唑基)-7$H$-苯并咪唑并[2、1-a]苯并[de]异喹啉-7-酮（2-O）和 2,5-二甲基-3-噻吩基）-7$H$-苯并咪唑并[2,1-a]苯并[de]异喹啉-7-酮（3-O）的合成，并研究了它们的光致变色特性。化合物 1-O 是由 2,5-二甲基噻吩-3-硼酸和 5-甲基-2-苯基噻唑-4-硼酸通过两个连续的铃木偶联反应合成的。光致变色化合物 2-O 和 3-O 是由 3-iodo-4-bromo-1,8-naphthalic anhydride 和 2,5-二甲基噻吩-3-硼酸或 2-苯基-5-甲基噻唑-4-硼酸通过多步反应制备的。所有光致变色化合物在乙酸乙酯溶液中经 365 纳米紫外线照射后，颜色都会从无色（或淡黄色）变为蓝绿色、紫色或橙色（取决于结构的性质）。将有色溶液置于波长为 530 纳米的可见光下，可将其还原为原来的无色（或淡黄色）溶液。
• Preparation and photochromic properties of 2,3-bisarylbenz[f]indenones
  作者：Mahmut Kose、Ersin Orhan、Kazushi Suzuki、Ahmet Tutar、Cihansel Sancak Ünlü、Yasushi Yokoyama

  DOI：10.1016/j.jphotochem.2013.01.012

  日期：2013.4

  From 2,3-dibromobenz[f]indenone, four compound: 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)benz[f]indenone 1O, 2,3-bis(3,5-dimethyl-4-isoxazolyl)benz[f]indenone 2O, 3-(3,5-dimethyl-4-isoxazolyl)-2-(5-methyl-2-phenyl-4-thiazolyl)benz[f]indenone 3O and 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)benz[f]indenol 4O were prepared, and their photochromic properties were investigated. Among them, photochrome 1O (weak

  由2,3-二溴苯并[ f ]茚满酮中的四种化合物：2,3-双（5-甲基-2-苯基-4-噻唑基）苯并[ f ]茚满酮1O，2,3-双（3,5-二甲基） -4-异恶唑基）苯[ n ]茚酮2O，3-（3,5-二甲基-4-异恶唑基）-2-（5-甲基-2-苯基-4-噻唑基）苯[ n ] 3O和2，制备了3-双（5-甲基-2-苯基-4-噻唑基）苯并[ f ]吲哚醇4O，并研究了它们的光致变色性能。其中，光致变色剂1O（弱光致变色）及其双噻唑基苯并[ f ]茚满醇衍生物4O显示光致变色现象。在闭环光反应期间，光致变色剂4O显示出高转化率（98.4％），而非对映异构体过量低（38％）。
• Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones
  作者：Ersin Orhan、Leyla Gundogdu、Mahmut Kose、Yasushi Yokoyama

  DOI：10.1016/j.jphotochem.2015.08.025

  日期：2016.1

  Six novel photochromic bisarylpyridazinones containing 2,5-dimethylthiophene or 5-methy1-2-phenylthiazole unit were synthesized, and their photochromic and fluorescence properties were investigated. The bisarylpyridazinones underwent reversible color change upon irradiation with UV or visible light. The effect of solvents on the absorption spectra of the bisarylpyridazinones was investigated. The closed-ring forms of bisarylpyridazinones displayed negative solvatochromism which was attributed to the high dipolar characters of the molecule. The open-ring forms of bisarylpyridazinones showed fluorescence at 400-480 nm upon excitation at 302 nm, and the intensities of emission bands gradually decreased during the ring-closing photoreactions. Among the synthesized bisarylpyridazinones, 4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-methyl(or 2-phenyl) pyridazin-3(2H)-ones (50 and 60) displayed rather large absorption and emission spectral change, higher quantum efficiency during the photoreaction compared to others. A high conversion ratio (94%) to the closed form was observed for 50. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis of photochromic 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone derivatives
  作者：Mahmut Kose、Çiğdem Yıldırım Şekerci、Kazushi Suzuki、Yasushi Yokoyama

  DOI：10.1016/j.jphotochem.2011.01.016

  日期：2011.3

  2,3-Bis(5-methyl-2-phenyl-4-thiazolyl)-1,4-naphthoquinone 1-O, its monoethylene acetal 2-O and methylated derivatives 3-O and 4-O were synthesized and their photochromic properties were investigated. While bisarylnaphthoquinone 1-O was nonphotochromic, its monoacetal 2-O and methylated derivatives 3-O and 4-O displayed good photochromism. Among them, the isomer 4-O recorded a remarkable diastereomeric excess (98.40%) with high conversion ratio (96.20%) upon UV irradiation. (C) 2011 Elsevier B.V. All rights reserved.