5-tert-butyl-1-[3-hydroxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane | 1426250-66-9

• 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: 5-tert-butyl-1-[3-hydroxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane
• 英文别名: 5-(5-Tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptan-1-yl)-2-(1-phenylbenzimidazol-2-yl)phenol
• CAS: 1426250-66-9
• 化学式: C₂₉H₃₀N₂O₄
• 分子量: 470.568
• InChiKey: CNYZGYSLAFNGNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-1-[3-hydroxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptane 以 均三甲苯 为溶剂， 生成 2,2,4,4-tetramethyl-3-oxopentyl 3-hydroxy-4-(N-phenylbenzimidazol-2-yl)benzoate
  参考文献：
  名称：

  带有 4-(benzazol-2-yl)-3-hydroxyphenyl 部分的双环二氧杂环丁烷在溶液和固态中的热化学发光

  摘要：

  带有 4-(benzothiazol-2-yl)-3-hydroxyphenyl 及其 4-(benzimidazol-2-yl) 类似物的四种双环二氧杂环丁烷的未催化热分解有效地引起了由于 ESIPT（激发态分子内质子转移）引起的热化学发光 (TCL)无论是在溶液中还是在固态中。TCL 的效率 (Φ TCL ) 在固态比在溶液中高约 15 倍。这种固态的高 Φ TCL 被认为是 TCL 几乎没有经历任何聚集引起的淬火的结果，因为基于发射体的 ESIPT 的大斯托克斯位移，并且因为 TCL 通过温度淬火减少很少，与解决方案中的案例。单线态化学激发效率 (Φ S) 似乎增加，达到峰值，然后随着反应温度的升高而降低。

  DOI：

  10.1016/j.tet.2023.133332
• 作为产物：
  描述：

  4-tert-butyl-5-[3-hydroxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-3,3-dimethyl-2,3-dihydrofuran 在 氧气 、 tetraphenylporphyrin 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以96%的产率得到5-tert-butyl-1-[3-hydroxy-4-(N-phenylbenzimidazol-2-yl)phenyl]-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

文献信息

• Notable Difference between Tetrabutylammonium Fluoride and Organic Superbases as Triggers for the Chemiluminescent Decomposition of Bicyclic Dioxetanes Bearing a 4-(N-Phenylbenzimidazol-2-yl)-3-hydroxyphenyl Moiety
  作者：Masakatsu Matsumoto、Nobuko Watanabe、Koh Kumagai、Rei Ohtuka、Ayu Wakatsuki、Hisako K. Ijuin、Yoshio Kabe

  DOI：10.3987/com-18-s(t)93

  日期：——

  Chemiluminescent decomposition of bicyclic dioxetanes 3a-3c bearing a 4-(N-phenylbenzimidazol-2-yl)-3-hydroxyphenyl moiety was effectively induced by organic superbases, BTPP [(tert-butylimino)tris(pyrrolidino)phosphorene], TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene), MTBD (7-methyl-1,5,7-tri azabicyclo [4.4.0] dec-5-ene), DBU (1,8-diazabicyclo-[5.4.0]-undec-7-ene), and TMG (tetramethylguanidine), as well as TBAF in acetonitrile. Dioxetane 3c bearing a 3,5-dihydroxyphenyl moiety showed diverse chemiluminescence profiles depending on the base used. BTPP caused chemiluminescent decomposition due to the di-oxido anion of dioxetane, while DBU and TMG induced chemiluminescence from the mono-oxido anion of dioxetane. On the other hand, TBAF caused effective chemiluminescence due to the mono-oxido anion, though it acted as a stronger base than BTPP with regard to the rate of decomposition of 3c.