6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol | 244124-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol
• 英文别名: 4-t-Butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran；6-(4-tert-butyl-3,3-dimethyl-2H-furan-5-yl)-2-phenyl-1,3-benzoxazol-4-ol
• CAS: 244124-49-0
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: BVJLHSRAIJVZAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 生成 6-(5-tert-Butyl-4,4-dimethyl-2,6,7-trioxa-bicyclo[3.2.0]hept-1-yl)-2-phenyl-benzooxazol-4-ol
  参考文献：
  名称：

  Base-induced chemiluminescence of 5- tert -butyl-1-(4-hydroxybenz[ d ]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes: chemiluminescence–chemiexcitation profile in aqueous medium

  摘要：

  Bicyclic dioxetanes bearing a 2-aryl-4-hydroxybenz[d]oxazol-6-yl moiety (3a-3c) and their 2-alkyl-analogs (3d, 3e) were synthesized. All these dioxetanes (3a-3e) afforded light with high efficiency on treatment with tetrabutylammonium fluoride in acetonitrile. In the NaOH-H2O system, chemiluminescence efficiency (Phi (CIEEL)) for alkyl-analogs (3d, 3e) decreased markedly, while Phi (CIEEL) for 3a-3c was still considerably high. Fluorescence study revealed that the marked decrease of (Phi (CIEEL)) for alkyl-analogs would be attributed to a synergetic effect of decreased chemiexcitation yield and fluorescence yield of the emitter in NaOH-H2O system. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01947-5
• 作为产物：
  描述：

  原苯甲酸三甲酯 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol
  参考文献：
  名称：

  Base-induced chemiluminescence of 5- tert -butyl-1-(4-hydroxybenz[ d ]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes: chemiluminescence–chemiexcitation profile in aqueous medium

  摘要：

  Bicyclic dioxetanes bearing a 2-aryl-4-hydroxybenz[d]oxazol-6-yl moiety (3a-3c) and their 2-alkyl-analogs (3d, 3e) were synthesized. All these dioxetanes (3a-3e) afforded light with high efficiency on treatment with tetrabutylammonium fluoride in acetonitrile. In the NaOH-H2O system, chemiluminescence efficiency (Phi (CIEEL)) for alkyl-analogs (3d, 3e) decreased markedly, while Phi (CIEEL) for 3a-3c was still considerably high. Fluorescence study revealed that the marked decrease of (Phi (CIEEL)) for alkyl-analogs would be attributed to a synergetic effect of decreased chemiexcitation yield and fluorescence yield of the emitter in NaOH-H2O system. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01947-5
• 作为试剂：
  描述：

  乙硫醇 、 N,N-二甲基甲酰胺 、 sodium;hydride 、 6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-4-methoxy-2-phenyl-benzooxazole 在 氮气 、 乙酸乙酯 、 氯化钠 、 magnesium sulfate anhydride 、 正己烷 、 6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol 作用下， 以 水 为溶剂， 反应 1.0h， 以to obtain 410 mg of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63])的产率得到6-(3-tert-Butyl-4,4-dimethyl-4,5-dihydro-furan-2-yl)-2-phenyl-benzooxazol-4-ol
  参考文献：
  名称：

  1,2-dioxetane derivative

  摘要：

  本发明的目的是提供一种化合物，不仅易于处理、热稳定且发射效率高，而且即使在质子溶剂中没有共存增强剂，也能显示高的发射效率。本发明涉及一种通式（I）的1,2-二氧杂环庚烷衍生物。其中，R1、R2、R3、R4和R5各自独立地表示氢、烷基或芳基；R2和R3的一对和R4和R5的一对可以分别结合形成环烷基。

  公开号：

  US06218135B1

文献信息

• US6218135B1
  申请人：——

  公开号：US6218135B1

  公开（公告）日：2001-04-17
• Base-induced chemiluminescence of 5- tert -butyl-1-(4-hydroxybenz[ d ]oxazol-6-yl)-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes: chemiluminescence–chemiexcitation profile in aqueous medium
  作者：Masakatsu Matsumoto、Yasuko Mizoguchi、Takuma Motoyama、Nobuko Watanabe

  DOI：10.1016/s0040-4039(01)01947-5

  日期：2001.12

  Bicyclic dioxetanes bearing a 2-aryl-4-hydroxybenz[d]oxazol-6-yl moiety (3a-3c) and their 2-alkyl-analogs (3d, 3e) were synthesized. All these dioxetanes (3a-3e) afforded light with high efficiency on treatment with tetrabutylammonium fluoride in acetonitrile. In the NaOH-H2O system, chemiluminescence efficiency (Phi (CIEEL)) for alkyl-analogs (3d, 3e) decreased markedly, while Phi (CIEEL) for 3a-3c was still considerably high. Fluorescence study revealed that the marked decrease of (Phi (CIEEL)) for alkyl-analogs would be attributed to a synergetic effect of decreased chemiexcitation yield and fluorescence yield of the emitter in NaOH-H2O system. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 1,2-dioxetane derivative
  申请人：Matsumoto Masakatsu

  公开号：US06218135B1

  公开（公告）日：2001-04-17

  The present invention has its objects to provide a compound not only which is easy to handle, thermally stable, and high in emission efficiency, but also which can show high emission efficiency without coexisting enhancer in the system even in a protic solvent. The present invention is related to a 1,2-dioxetane derivative of general formula (I). [wherein R1, R2, R3, R4 and R5 each independently represents hydrogen, alkyl or aryl; a pair of R2 and R3 and a pair of R4 and R5 may respectively be joined to each other to form a cycloalkyl group.

  本发明的目的是提供一种化合物，不仅易于处理、热稳定且发射效率高，而且即使在质子溶剂中没有共存增强剂，也能显示高的发射效率。本发明涉及一种通式（I）的1,2-二氧杂环庚烷衍生物。其中，R1、R2、R3、R4和R5各自独立地表示氢、烷基或芳基；R2和R3的一对和R4和R5的一对可以分别结合形成环烷基。