2-nonafluorobutylbenzimidazole | 115525-76-3

• 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: 2-nonafluorobutylbenzimidazole
• 英文别名: 2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1H-benzimidazole
• CAS: 115525-76-3
• 化学式: C₁₁H₅F₉N₂
• 分子量: 336.16
• InChiKey: CTJYGNKTMZKLHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-nonafluorobutylbenzimidazole 在 溴 作用下， 以 水 为溶剂， 反应 24.0h， 以37%的产率得到4,5,6,7-Tetrabromo-2-nonafluorobuthylbenzimidazole
  参考文献：
  名称：

  Polyhalogenobenzimidazoles: synthesis and Their inhibitory activity against casein kinases

  摘要：

  A series of novel polyhalogenated benzimidazoles have been prepared by exhaustive bromination of a variety of 2-substituted benzimidazoles. The efficacy of both new compounds and a number of their previously described cognates as inhibitors of casein kinases CK1, CK2 and G-CK was investigated. The type of N-1 alkyl substituent as well as introduction of a polyfluoroalkyl moiety at position 2 did not markedly influence the inhibitory efficacy toward CK2 of the respective 4,5,6,7-tetra-bromobenzimidazole derivatives which conversely were almost ineffective toward CK1 and G-CK. However, 4,5,6,7-tetra-bromobenzimidazoles substituted at position 2 with either chlorine, bromine or sulfur atom, while manifesting a still considerable inhibitory activity against CK2 (IC50 in the 0.49-0.93 muM range) proved to be potentially powerful inhibitors also against CK1 (IC50 in the 18.4-2.2 muM range). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00403-6
• 作为产物：
  描述：

  lithium 4,4,5,5,6,6,7,7,7-nonafluoro-1-oxo-1-phenylhept-2-en-3-olate 在 溶剂黄146 、 sodium nitrite 作用下， 生成 3-hydroximino-2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-4-phenyl-3H-1,5-benzodiazepine 、 2-nonafluorobutylbenzimidazole
  参考文献：
  名称：

  Reactions of 3-(Polyfluoroalkyl)propane-1,2,3-trione-2-oximes with Diaminoarenes

  摘要：

  Novel quinoxaline derivatives have been synthesized via the reaction of 3-trifhioromethyl-1,2,3-propanetrione-2-oximes with 1,2-diaminobenzene or 2,3-diaminonaphthalene: 2-trifluoromethyl-3-aroylquinoxaline and 2-trifluoromethyl-3-aroylbenzo[g]quinoxaline. Under similar conditions, 3-R-F-1,2,3-propanetrione-2-oximes [R-F = C3F7, H(CF2)(4), C4F9, and C6F13] with the same diaminoarenes have given a mixture of the condensation and fragmentation products in different ratios. The structure of (4-methylphenyl)[3-(tri-fluoromethyl)benzo[g]quinoxalin-2-yl]methanone has been elucidated by means of X-ray diffraction analysis.

  DOI：

  10.1134/s1070363219030083

文献信息

• Synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxylates. Reactions with nucleophiles
  作者：O. G. Kuzueva、Ya. V. Burgart、V. I. Saloutin、O. N. Chupakhin

  DOI：10.1007/bf02494751

  日期：1999.10

  Fluorine-containing alkyl 2-cyano-3-oxocarboxylates were synthesized for the first time by the reaction of ethyl cyanoacetate with fluorine-substituted carboxylic acid halides or alkyl carboxylates. The reactions with hydrazine hydrate, phenylhydrazine, ando-phenylenediamine give hydrazinium (ammonium) enolates or products of acid decomposition.

  通过氰基乙酸乙酯与氟取代的羧酸卤化物或烷基羧酸酯反应，首次合成了含氟的2-氰基-3-氧代羧酸烷基酯。与水合肼、苯肼和邻苯二胺反应生​​成肼鎓（铵）烯醇化物或酸分解产物。
• Synthesis and Antimicrobial Activities of New Polyhalogenated Benzimidazoles
  作者：Agnieszka E. Laudy、Rosa Moo-Puc、Roberto Cedillo-Rivera、Zygmunt Kazimierczuk、Andrzej Orzeszko

  DOI：10.1002/jhet.936

  日期：2012.9

  A series of new polyhalogenated benzimidazoles has been synthesized and their antibacterial and antiprotozoal activity was evaluated. Several of new substituted halogenobenzimidazoles and their 2′‐deoxynucleosides showed noteworthy antiprotozoal toxicity particularly against Giardia lamblia. The most potent agents against bacteria and fungi were 4,5,6,7‐tetrachlorobenzimidazoles with polyfluoroalkyl

  合成了一系列新型的多卤代苯并咪唑，并评估了它们的抗菌和原生动物活性。几种新的取代的卤代苯并咪唑及其2'-脱氧核苷显示出显着的抗原生动物毒性，尤其是对兰氏贾第鞭毛虫。对细菌和真菌最有效的药剂是在杂环的第2位具有多氟烷基链的4,5,6,7-四氯苯并咪唑。
• Fluoroalkyl-containing ?,?'-tricarbonyl compounds: Tautomerism and reaction with N-nucleophiles
  作者：V. M. Krokhalev、V. I. Saloutin、A. D. Romas'、B. A. Ershov、K. I. Pashkevich

  DOI：10.1007/bf00960661

  日期：1990.2
• Reaction of 2-halofluoroalkyl-containing ?-ketoesters with N-dinucleophiles
  作者：K. I. Pashkevich、Z. E. Skryabina、V. I. Saloutin

  DOI：10.1007/bf00957313

  日期：1987.11
• KROXALEV, V. M.;SALOUTIN, V. I.;ROMAS, A. D.;ERSHOV, B. A.;PASHKEVICH, K.+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 376-382
  作者：KROXALEV, V. M.、SALOUTIN, V. I.、ROMAS, A. D.、ERSHOV, B. A.、PASHKEVICH, K.+

  DOI：——

  日期：——