(3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate | 74451-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate
• 英文别名: (5-Methyl-2-phenylpyrazol-3-yl) 4-chlorobenzoate
• CAS: 74451-91-5
• 化学式: C₁₇H₁₃ClN₂O₂
• 分子量: 312.755
• InChiKey: UUJUJDCXSHLCJS-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate 在 potassium carbonate 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.5h， 生成 (5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chlorophenyl)methanone
  参考文献：
  名称：

  Synthesis, Structure, and Biological Activities of [5-(Arylthio/sulfinyl/sulfonyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-arylmethanones

  摘要：

  A series of novel N-phenylpyrazolyl aryl methanones derivatives containing the arylthio/sulfinyl/sulfonyl group have been synthesized via multi-step reactions from 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and characterized by melting point, H-1 NMR, C-13 NMR, FT-IR, and HRMS. The crystal structure of (5-(4-chlorophenylsulfonyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone containing the arylsulfonyl moiety is reported. The biological activity results showed that some of the title compounds exhibit favorable herbicidal and insecticidal activities.

  DOI：

  10.1080/10426507.2014.919503
• 作为产物：
  描述：

  苯肼 在 1,1-二氯乙烷 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (3-methyl-1-phenyl-1H-pyrazol-5-yl) 4-chlorobenzoate
  参考文献：
  名称：

  Synthesis, Structure, and Biological Activities of [5-(Arylthio/sulfinyl/sulfonyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-arylmethanones

  摘要：

  A series of novel N-phenylpyrazolyl aryl methanones derivatives containing the arylthio/sulfinyl/sulfonyl group have been synthesized via multi-step reactions from 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and characterized by melting point, H-1 NMR, C-13 NMR, FT-IR, and HRMS. The crystal structure of (5-(4-chlorophenylsulfonyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone containing the arylsulfonyl moiety is reported. The biological activity results showed that some of the title compounds exhibit favorable herbicidal and insecticidal activities.

  DOI：

  10.1080/10426507.2014.919503

文献信息

• O‐Acylation of 3‐Methylpyrazol‐5‐ones with Acylisothiocyanates
  作者：Mykhaylo V. Vovk、Andrij V. Bol'but、Pavlo S. Lebed'

  DOI：10.1081/scc-120030702

  日期：2004.12.31

  Abstract 3‐Methylpyrazol‐5‐ones 1 react by the O‐acylation pattern with acylisothiocyanates 2 in the solvent mixture ethanol–dioxane in the presence of the equimolar amount of potassium hydroxide to produce 5‐acyloxy‐3‐methyl‐1H‐pyrazoles 3.

  摘要 在等摩尔量的氢氧化钾存在下，3-甲基吡唑-5-酮 1 通过 O-酰化模式与酰基异硫氰酸酯 2 在溶剂混合物乙醇-二恶烷中反应，生成 5-酰氧基-3-甲基-1H-吡唑 3 .
• Synthesis of 1-acyl-1,2-dihydro-3<i>H</i>-pyrazol-3-ones<i>VIA</i>lewis acid-mediated rearrangement of 3-acyloxypyrazoles
  作者：Hiroshi Maruoka、Kenji Yamagata、Fumi Okabe、Yukihiko Tomioka

  DOI：10.1002/jhet.5570430408

  日期：2006.7

  The unusual formation of 1-acyl-1,2-dihydro-3H-pyrazol-3-ones starting from 3-acyloxypyrazoles by Fries-type rearrangement is described. Under normal conditions, acylation of 2,4-dihydro-3H-pyrazol-3-ones 1 and 2 with acid chlorides or anhydrides in the presence of triethylamine gave the corresponding 3-acyloxypyrazoles 3a-f and 4a-f. Treatment of 3a-c and 4a-f with Lewis acid, e.g. titanium(IV) chloride

  描述了通过弗里斯类型重排从3-酰氧基吡唑开始的1-酰基-1,2-二氢-3 H-吡唑-3-酮的不寻常形成。在正常条件下，在三乙胺存在下用酰氯或酸酐将2，4-二氢-3 H-吡唑-3-酮1和2酰化，得到相应的3-酰氧基吡唑3a-f和4a-f。用路易斯酸，例如氯化钛（IV）和氯化锡（IV）处理3a-c和4a-f，导致酰基迁移，得到相应的1-酰基-1,2-二氢-3 H-吡唑- 3位5a-c和6a-f。有趣的是，3-酰氧基吡唑3e和3f与氯化锡（IV）的反应提供了相应的锡（IV）配合物8e和8f。
• RAPID MICROWAVE-ENHANCED SYNTHESIS OF 1-PHENYL-3-METHYL- 5-ACYLOXYPYRAZOLES UNDER SOLVENT-FREE CONDITIONS
  作者：Yinjuan Bai、Jun Lu、Haiying Gan、Zhenjun Wang

  DOI：10.1081/scc-120005938

  日期：2002.1

  The microwave-enhanced synthesis of 5-acyloxypyrazoles from 1-phenyl-3-methylpyrazole-5-one and acid chlorides under solvent-free conditions has been achieved in moderate to good yield.
• TEREBENINA, A.;JORDANOV, N.;JORDANOV, B.;BORISSOV, G., IZV. XIM. BAN, 1981, 14, N 1, 118-124
  作者：TEREBENINA, A.、JORDANOV, N.、JORDANOV, B.、BORISSOV, G.

  DOI：——

  日期：——