4-tert-butyl-5-{4-[N-(4-carboxybutyl)benzimidazol-2-yl]-3-hydroxyphenyl}-3,3-dimethyl-2,3-dihydrofuran | 1426250-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-tert-butyl-5-{4-[N-(4-carboxybutyl)benzimidazol-2-yl]-3-hydroxyphenyl}-3,3-dimethyl-2,3-dihydrofuran
• CAS: 1426250-62-5
• 化学式: C₂₈H₃₄N₂O₄
• 分子量: 462.589
• InChiKey: VURXGEHJUTVRCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.58
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-5-{4-[N-(4-carboxybutyl)benzimidazol-2-yl]-3-hydroxyphenyl}-3,3-dimethyl-2,3-dihydrofuran 在 氧气 、 tetraphenylporphyrin 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以99%的产率得到5-tert-butyl-1-{4-[N-(4-carboxybutyl)benzimidazol-2-yl]-3-hydroxyphenyl}-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
  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 在 正丁基锂 、 三氟甲磺酸酐 、 sodium hydride 、 三苯基氧化膦 、 sodium thiomethoxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 4-tert-butyl-5-{4-[N-(4-carboxybutyl)benzimidazol-2-yl]-3-hydroxyphenyl}-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