4-[2-(3-chlorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one | 1415650-69-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[2-(3-chlorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one
• 英文别名: 4-[2-(3-chlorophenyl)hydrazinyl]-5-methylpyrazol-3-one
• CAS: 1415650-69-9
• 化学式: C₁₀H₉ClN₄O
• 分子量: 236.661
• InChiKey: GDVVPCOYCZPLHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.85
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[2-(3-chlorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.25h， 以83%的产率得到4-[2-(3-chlorophenyl)hydrazono]-3-methyl-1-(prop-2-ynyl)-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  新型吡唑啉酮和吡唑啉酮核苷的合成及抗菌评价

  摘要：

  描述了一系列新的4-芳基肼基-5-甲基-1，2-二氢吡唑-3-酮4a–h以及它们的N 2-烷基和无环，吡喃吡喃糖基和呋喃呋喃糖基衍生物的合成。K2CO3用烯丙基溴，炔丙基溴，乙酸4-溴丁酯，2-乙酰氧基乙氧基甲基溴和2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴在4a–h上进行烷基化吡唑啉酮环的2位。在Vorbruggen糖基化条件下用1,2,3,5-四-O-乙酰基-β-D-呋喃呋喃糖将4a糖基化，得到相应的N 2-4-芳基肼基吡唑啉酮呋喃糖苷9a，收率良好。乙酰基保护的核苷的常规脱保护以良好的产率提供了相应的4-芳基肼基吡唑啉酮核苷。筛选了一些新合成的化合物的抗微生物活性。化合物4b，12a和14d对黄曲霉，青霉属和大肠杆菌具有中等活性。

  DOI：

  10.1080/15257770.2012.732250
• 作为产物：
  描述：

  diethyl 3,3'-[ethane-1,2-diylbis(azan-1-yl-1-ylidene)]bis(2-[2-(3-chlorophenyl)hydrazono]butanoate) 在 哌啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以55%的产率得到4-[2-(3-chlorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Convenient Synthesis of Novel Bis(hydrazone) and Bis(indole) Derivatives

  摘要：

  The synthetic potency of (Z,Z)-3,3'-(ethane-1,2-diyldiimino)-dibut-2-enoate (1) as a versatile precursors for the synthesis of novel bis(hydrazone) and bis(indole) derivatives via its reaction with some electrophiles and nitrogen nuclephiles was investigated.

  DOI：

  10.3987/com-08-11615

文献信息

• Two neoteric pyrazole compounds as potential anti-cancer agents: Synthesis, electronic structure, physico-chemical properties and docking analysis
  作者：Renjith Thomas、Y. Sheena Mary、K.S. Resmi、B. Narayana、B.K. Sarojini、G. Vijayakumar、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2019.01.003

  日期：2019.4

  The pyrazole derivatives, (E)-4-(2-(3-chlorophenyl)hydrazono)-5-methyl-2,4-dihydro-3H-pyrazol-3-one (CPHMP) and 4-(2-(2,4,5-trichlorophenyl)hydrazinyl)-2,4-dihydro-3H-pyrazol-3-one (TCPHP) were synthesized and identified using LCMS (ESI-MS), C H N elemental and NMR analysis. Using FT-IR and FT-Raman spectra were recorded and compared with theoretically simulated spectra and found that both of them agrees with each other. The oscillator strength of CPHMP is sufficiently large which makes it an ideal candidate to use as a photo sensitizer in photo voltaic systems. First hyperpolarizabilities of CPHMP and TCPHP are 94.04 and 50.52 times that of urea. From the MEP plot the active sites are determined and C=0 group and NH moiety are the most electrophilic and nucleophilic regions for both the pyrazole derivatives. Docking studies propose that CPHMP and TCPHP might reveal negative response against human microsomal prostaglandin E synthase 1. (C) 2019 Elsevier B.V. All rights reserved.