6,6-Dimethyl-4,5,6,7-tetrahydro-4-oxo-3-phenylamino-1H-indazol | 51924-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-Dimethyl-4,5,6,7-tetrahydro-4-oxo-3-phenylamino-1H-indazol
• 英文别名: 3-(phenylamino)-6,6-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one；3-anilino-6,6-dimethyl-1,5,6,7-tetrahydro-indazol-4-one；6,6-dimethyl-3-(phenylamino)-4,5,6,7-tetrahydro-1H-indazol-4-one；3-anilino-6,6-dimethyl-5,7-dihydro-1H-indazol-4-one
• CAS: 51924-82-4
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: XDJDOSFSATWLCA-UHFFFAOYSA-N

物化性质

• 熔点：
  274-277 °C(Solv: ethanol (64-17-5))
• 沸点：
  459.3±45.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,6-Dimethyl-4,5,6,7-tetrahydro-4-oxo-3-phenylamino-1H-indazol 、 乙酰乙酸乙酯 在 溶剂黄146 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of Some New Thiazole, Thiophene, and 2,3-Dihydro-1,3,4-thiadiazole and Pyrimidino[1,2-b]indazole Derivatives

  摘要：

  Hydrazonoyl halides 4a-g reacted with methyl carbodithioate 3 thioanilide 10 to give 1,3,4-thiadiazoles 5a-g and 13a-g, respectively. Thioanilide 10 reacted with omega-bromoacetophenones 14a-e to give the acyclic product 15a-e, which was converted to the thiophenes 16a-e and to the thiazoles 17a-e, respectively. Structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthesis route whenever possible.

  DOI：

  10.1080/104265090921083
• 作为产物：
  描述：

  2-amino-4,4-dimethyl-6-oxo-N-phenylcyclohex-1-enecarbothioamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以51%的产率得到6,6-Dimethyl-4,5,6,7-tetrahydro-4-oxo-3-phenylamino-1H-indazol
  参考文献：
  名称：

  Suesse, M.; Johne, S., Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 4, p. 635 - 639

  摘要：

  DOI：

文献信息

• One‐Pot Synthesis and Antiproliferative Activity of Highly Functionalized Pyrazole Derivatives
  作者：Matteo Lusardi、Chiara Rotolo、Marco Ponassi、Erika Iervasi、Camillo Rosano、Andrea Spallarossa

  DOI：10.1002/cmdc.202100670

  日期：2022.3.4

  one-pot, regioselective and versatile procedure was developed for the synthesis of a series of highly functionalized pyrazole derivatives. The compounds were tested for antiproliferative activity on a panel of tumour and normal cells. 5-anilino-4-nitrile-3-phenyl pyrazoles emerged as the most promising derivatives, and compound 23 selectively inhibited the growth of estrogen-dependent SKMEL-28 and HeLa

  开发了一种一锅法、区域选择性和通用的方法来合成一系列高度官能化的吡唑衍生物。测试了这些化合物对一组肿瘤和正常细胞的抗增殖活性。5-苯胺-4-腈-3-苯基吡唑是最有希望的衍生物，化合物23选择性地抑制雌激素依赖性SKMEL-28和HeLa细胞的生长。对接模拟计算了 ERα- 23和 ERβ- 23复合物的微摩尔K i值，表明雌激素受体是这一系列吡唑的潜在生物学靶标。
• A Simple and Efficient Diversity-Oriented Synthesis of New Substituted 3-(Arylamino)-6,7-dihydro-1H-indazol-4(5H)-ones by a KOH-Assisted One-Pot Reaction
  作者：Mehdi Rimaz、Behzad Khalili、Golaleh Khatyal、Hossein Mousavi、Farkhondeh Aali

  DOI：10.1071/ch17146

  日期：——

  A novel, simple, and straightforward combinatorial method for the synthesis of new substituted 3-(arylamino)-6,7-dihydro-1H-indazol-4(5H)-one derivatives has been developed. The synthesis was achieved via a one-pot three-component reaction of aromatic isothiocyanates, substituted 1,3-cyclohexanediones, and hydrazine hydrate in dimethyl sulfoxide as a polar aprotic solvent. This methodology has the

  一种新颖的，简单的，并为新的取代的3-（芳基氨基）合成直接的组合方法-6,7-二氢-1- ħ -吲唑-4（5 ħ） -酮衍生物已被开发出来。通过芳族异硫氰酸酯，取代的1,3-环己二酮和水合肼在作为极性非质子溶剂的二甲亚砜中进行一锅三组分反应来完成合成。该方法的优点是反应条件温和，收率高至优异，原料易得，操作简单且易于后处理。该化学方法为3-芳基氨基吲唑骨架的多样性导向构建提供了有效的合成策略。
• Spectroscopic, X-ray and DFT studies of prototropic tautomerism and photophysical properties of regioselectively designed new 3-, 2,3-substituted tetrahydro[4H]indazol-4-ones
  作者：Jasneet Rana、R.P. Chaudhary

  DOI：10.1016/j.molstruc.2021.130762

  日期：2021.11

  prototropic tautomerism studies of 3-substituted-2H-indazol-4-ones have been described on the basis of spectral, LC-MS and DFT studies. The structural ambiguity was resolved by X-ray diffraction studies of compound 5 and validated by theoretical studies on the structure 5a and its regioisomer 6a. Photophysical studies (UV and fluorescence) of compounds 3 and 5 in different solvents are also reported

  二甲酮和异硫氰酸芳基酯在三乙胺中反应生成硫代酰胺2，其与肼或苯肼缩合生成 3-取代-2 H-吲唑3或 2,3-二取代-2 H-吲唑5，分别代替预期的区域异构体 3-取代的-1 H-吲唑4或 1,3-二取代的-1 H-吲唑6.光谱数据（IR、NMR 和质量）对结构区分几乎没有帮助。3-取代-2 H的质子互变异构研究-indazol-4-ones 已经在光谱、LC-MS 和 DFT 研究的基础上进行了描述。结构模糊性通过化合物5的 X 射线衍射研究解决，并通过对结构5a及其区域异构体6a 的理论研究进行验证。还报告了化合物3和5在不同溶剂中的光物理研究（紫外线和荧光）。
• SUESSE M.; JOHNE S., J. PRAKT. CHEM., 328,(1986) N 4, 635-639
  作者：SUESSE M.、 JOHNE S.

  DOI：——

  日期：——
• Synthesis of Some New Thiazole, Thiophene, and 2,3-Dihydro-1,3,4-thiadiazole and Pyrimidino[1,2-b]indazole Derivatives
  作者：Nora M. Rateb

  DOI：10.1080/104265090921083

  日期：2005.10

  Hydrazonoyl halides 4a-g reacted with methyl carbodithioate 3 thioanilide 10 to give 1,3,4-thiadiazoles 5a-g and 13a-g, respectively. Thioanilide 10 reacted with omega-bromoacetophenones 14a-e to give the acyclic product 15a-e, which was converted to the thiophenes 16a-e and to the thiazoles 17a-e, respectively. Structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthesis route whenever possible.