6,6-dimethyl-3-perfluoroethyl-1-phenyl-6,7-dihydro-1H-indazol-4(5H)-one | 1373316-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6,6-dimethyl-3-perfluoroethyl-1-phenyl-6,7-dihydro-1H-indazol-4(5H)-one
• CAS: 1373316-08-5
• 化学式: C₁₇H₁₅F₅N₂O
• 分子量: 358.311
• InChiKey: SYQIKCZZKNVNNB-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-3-perfluoroethyl-1-phenyl-6,7-dihydro-1H-indazol-4(5H)-one 在 吡啶 、 selenium(IV) oxide 、 盐酸羟胺 、 溶剂黄146 作用下， 反应 23.0h， 生成 (Z)-5-(hydroxyimino)-6,6-dimethyl-1-phenyl-3-perfluoroethyl-1,5,6,7-tetrahydro-4H-indazol-4-one
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Fluorine-Containing 6,7-Dihydroindazolone and 6,7-Dihydrobenzisoxazolone Derivatives

  摘要：

  含氟的 6,7-二氢吲唑-4,5-二酮和 6,7-二氢苯并异噁唑-4-5-二酮、5-[3-氟苯甲酰氧基亚氨基)]-6,6-二甲基-3-(3-氟苯基)-6、7-二氢苯并[d]]异恶唑-4(5H)-酮和 5,5-二甲基-7-苯基-9-(4-氟苯基)-3,5,6,7-四氢-2H-吡唑并[4,3-f]喹喔啉的合成。测定了这些化合物对细胞株 MCF-7（人类乳腺癌）和 HepG2（人类肝细胞癌）的细胞毒活性。这里合成的含氟 6,7-二氢吲唑酮衍生物包括具有明显抗增殖活性的物质，其机制可能与诱导凋亡有关，诱导凋亡的原因是正常细胞周期受到破坏，即肿瘤细胞延迟进入 G2/M 期。

  DOI：

  10.1007/s11094-020-02258-z

文献信息

• Synthesis of perfluoroalkyl-substituted 4,5-dihydro-3H-pyrazolo[4,3-a]phenazines and tetrahydroimidazo[4,5-e]indazoles
  作者：T. S. Khlebnikova、Yu. A. Piven’、A. V. Baranovskii、F. A. Lakhvich

  DOI：10.1134/s1070428013030184

  日期：2013.3

  Oxidation of 1-aryl-3-perfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones with selenium dioxide in the presence of sulfuric acid in glacial acetic acid, followed by treatment of 6,7-dihydro-1H-indazole-4,5-diones thus obtained with an equimolar amount of o-phenylenediamine in ethanol or with a mixture of 4-fluorobenzaldehyde and ammonium acetate in acetic acid, gave 3-aryl-1-perfluoroalkyl-4,5-dihydro-3H-pyrazolo-[4

  在冰醋酸中有硫酸存在下，用二氧化硒氧化1-芳基-3-全氟烷基-6,7-二氢-1 H-吲唑-4（5 H）-ones，然后处理6,7-用乙醇中等摩尔量的邻苯二胺或乙酸中4-氟苯甲醛和乙酸铵的混合物制得二氢-1 H-吲唑-4,5-二酮，得到3-芳基-1-全氟烷基-4， 5-二氢-3 H-吡唑并-[4,3- a ]吩嗪和6-芳基-2-（4-氟苯基）-8-全氟烷基-1（3），4,5,6-四氢咪唑并[4,5 - ë ]吲唑，分别。
• Synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage
  作者：Tatyana S. Khlebnicova、Yuri A. Piven、Alexander V. Baranovsky、Fedor A. Lakhvich、Svetlana V. Shishkina、Daina Zicāne、Zenta Tetere、Irisa Rāviņa、Viktors Kumpiņš、Inese Rijkure、Inese Mieriņa、Uldis Peipiņš、Māris Turks

  DOI：10.1016/j.steroids.2016.08.002

  日期：2017.1

  An efficient protocol for the synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage has been developed from naturally accessible precursor betulin. For the first time a series of betulonic acid-indazolone hybrids have been synthesized via an acylation of corresponding 6,7-dihydro-1H-indazol-4(5H)-one oximes with betulonic acid chloride. Diastereoselective reduction of the obtained betulonic acid conjugates with NaBH4 resulted in a formation of betulinic acid-indazolone hybrids in excellent yields. The configuration of the key compounds has been fully established by X-ray and 2D NMR analysis. (C) 2016 Elsevier Inc. All rights reserved.
• Synthesis and transformations of perfluoroalkyl-containing 6,7-dihydro-1H-indazol-4(5H)-ones oximes
  作者：T. S. Khlebnikova、Yu. A. Piven’、A. V. Baranovskii、F. A. Lakhvich

  DOI：10.1134/s1070428015050115

  日期：2015.5

  Refluxing 3-perfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones with 4-fold excess of hydroxylamine hydrochloride in pyridine afforded their (E)-oximes. The obtained oximes were alkylated with ethyl iodide and acylated with carboxylic acids chlorides to obtain (E)-O-alkyl- and (E)-O-acyloximes respectively. Heating oximes in PPA at 120A degrees C results in their aromatization by Semmler-Wolff reaction, hydrolysis of perfluoroalkyl groups, and generation of 4-amino-1-aryl-5,6-dimethyl-1H-indazole-3-carboxylic acids from of 3-tri-fluoromethylindazolone oximes and 1-(4-amino-1-aryl-5,6-dimethyl-1H-indazol-3-yl)-fluoroalkan-1-ones from of 3-perfluoroethyl- and 3-perfluoropropylindazolone oximes.
• Regioselective synthesis of polyfluoroalkyl-substituted 7-(1H-1,2,3-triazol-1-yl)-6,7-dihydro-1H-indazol-4(5H)-ones
  作者：T. S. Khlebnikova、Yu. A. Piven’、A. V. Baranovskii、F. A. Lakhvich

  DOI：10.1134/s1070428012030128

  日期：2012.3

  3-Polyfluoroalkyl-6,6-dimethyl-7-(1H-1,2,3-triazol-1-yl)-6,7-dihydro-1H-indazol-4(5H)-ones were synthesized with high regioselectivity by 1,3-dipolar cycloaddition of terminal alkynes (phenylacetylene, hex-1-yne, hept-1-yne, and but-3-yn-1-ol) to 7-azido-6,6-dimethyl-3-polyfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones which were prepared by bromination of 6,6-dimethyl-3-polyfluoroalkyl-6,7-dihydro-1H-indazol-4(5H)-ones with N-bromosuccinimide in anhydrous carbon tetrachloride, followed by treatment of the corresponding 7-bromo derivatives with sodium azide.