5-(4-carboxy-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran | 244124-41-2

• 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: 5-(4-carboxy-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran
• 英文别名: 4-(4-tert-butyl-3,3-dimethyl-2H-furan-5-yl)-2-methoxybenzoic acid
• CAS: 244124-41-2
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: YVHJPZSBBMSHKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-carboxy-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran 在 三氟甲磺酸酐 、 氧气 、 tetraphenylporphyrin 、 三苯基氧化膦 、 sodium thiomethoxide 作用下， 以 二氯甲烷 、 对二甲苯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.0h， 生成 2,2,4,4-tetramethyl-3-oxopentyl 4-(benzimidazol-2-yl)-3-hydroxybenzoate
  参考文献：
  名称：

  Synthesis of Bicyclic Dioxetanes Bearing a 4-(Benzimidazol-2-yl)-3-hydroxyphenyl Group and Their Base-Induced Chemiluminescent Decomposition in an Aprotic Medium and in an Aqueous Medium

  摘要：

  Bicyclic dioxetane, 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane, bearing a 4-(benzimidazol-2-yl)-3-hydroxyphenyl group at the 1-position and its N-substituted benzimidazolyl-analogs were synthesized. N-Methylbenzimidazolyl-analog and N-phenylbenzimidazolyl-analog were found to undergo charge-transfer-induced decomposition (CTID) to effectively give light in both TBAF/MeCN and in NaOH/H2O. The CTID of N-(4-carboxybutyl)benzimidazolyl-analog gave also effectively light both in MeCN and in H2O. On the other hand, chemiluminescent CTID of the unsubstituted benzimidazolyl-analog changed depending on the base used: TBAF/MeCN induced weak emission of yellow light due to a dianion of the dioxetane, while TMG(tetramethylguanidine)/MeCN induced strong emission of blue light due to a monoanion of the dioxetane.

  DOI：

  10.3987/com-12-12602
• 作为产物：
  描述：

  5-(4-bromo-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran 、 二氧化碳 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以87%的产率得到5-(4-carboxy-3-methoxyphenyl)-4-tert-butyl-3,3-dimethyl-2,3-dihydrofuran
  参考文献：
  名称：

  Synthesis of Bicyclic Dioxetanes Bearing a 4-(Benzimidazol-2-yl)-3-hydroxyphenyl Group and Their Base-Induced Chemiluminescent Decomposition in an Aprotic Medium and in an Aqueous Medium

  摘要：

  Bicyclic dioxetane, 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane, bearing a 4-(benzimidazol-2-yl)-3-hydroxyphenyl group at the 1-position and its N-substituted benzimidazolyl-analogs were synthesized. N-Methylbenzimidazolyl-analog and N-phenylbenzimidazolyl-analog were found to undergo charge-transfer-induced decomposition (CTID) to effectively give light in both TBAF/MeCN and in NaOH/H2O. The CTID of N-(4-carboxybutyl)benzimidazolyl-analog gave also effectively light both in MeCN and in H2O. On the other hand, chemiluminescent CTID of the unsubstituted benzimidazolyl-analog changed depending on the base used: TBAF/MeCN induced weak emission of yellow light due to a dianion of the dioxetane, while TMG(tetramethylguanidine)/MeCN induced strong emission of blue light due to a monoanion of the dioxetane.

  DOI：

  10.3987/com-12-12602

文献信息

• 1,2-dioxetane derivative
  申请人：FUJIREBIO INC.

  公开号：EP0943618A2

  公开（公告）日：1999-09-22

  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不仅易于处理、热稳定性好、发射效率高，而且即使在质子溶剂中也能在体系中不共存增强剂的情况下显示出高发射效率的化合物。 本发明涉及通式（I）的 1，2-二氧杂环丁烷衍生物。 [其中 R1、R2、R3、R4 和 R5 各自独立地代表氢、烷基或芳基；一对 R2 和 R3 以及一对 R4 和 R5 可分别相互连接形成环烷基。
• US6218135B1
  申请人：——

  公开号：US6218135B1

  公开（公告）日：2001-04-17
• Synthesis of Bicyclic Dioxetanes Bearing a 4-(Benzimidazol-2-yl)-3-hydroxyphenyl Group and Their Base-Induced Chemiluminescent Decomposition in an Aprotic Medium and in an Aqueous Medium
  作者：Masakatsu Matsumoto、Hiromasa Hagiwara、Nobuko Watanabe、Hisako K. Ijuin、Masashi Yamada

  DOI：10.3987/com-12-12602

  日期：——

  Bicyclic dioxetane, 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane, bearing a 4-(benzimidazol-2-yl)-3-hydroxyphenyl group at the 1-position and its N-substituted benzimidazolyl-analogs were synthesized. N-Methylbenzimidazolyl-analog and N-phenylbenzimidazolyl-analog were found to undergo charge-transfer-induced decomposition (CTID) to effectively give light in both TBAF/MeCN and in NaOH/H2O. The CTID of N-(4-carboxybutyl)benzimidazolyl-analog gave also effectively light both in MeCN and in H2O. On the other hand, chemiluminescent CTID of the unsubstituted benzimidazolyl-analog changed depending on the base used: TBAF/MeCN induced weak emission of yellow light due to a dianion of the dioxetane, while TMG(tetramethylguanidine)/MeCN induced strong emission of blue light due to a monoanion of the dioxetane.