吡喃并[4,3-c]吡唑-4(2H)-酮,2-(4-氯苯基)-3,6-二甲基- | 106089-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 吡喃并[4,3-c]吡唑-4(2H)-酮,2-(4-氯苯基)-3,6-二甲基-
• 英文名称: 2-(4-chlorophenyl)-3,6-dimethylpyrano<4,3-c>pyrazol-4(2H)-one
• 英文别名: 3,6-dimethyl-2-(4-chlorophenyl)pyrano[4,3-c]pyrazol-4(2H)-one；2-(4-Chlorophenyl)-3,6-dimethylpyrano[4,3-c]pyrazol-4(2H)-one；2-(4-chlorophenyl)-3,6-dimethylpyrano[4,3-c]pyrazol-4-one
• CAS: 106089-52-5
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: DIXPKYLMLGZSCG-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C(Solv: methanol (67-56-1))
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  去氢乙酸 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 95.5h， 生成 吡喃并[4,3-c]吡唑-4(2H)-酮,2-(4-氯苯基)-3,6-二甲基-
  参考文献：
  名称：

  从脱氢乙酸合成 Pyrano[4,3-c]pyrazol-4(1H)-ones 和 -4(2H)-ones。用于明确结构分配的同核和异核选择性 NOE 测量

  摘要：

  脱氢乙酸 N-取代腙环化得到 1-取代 3,6-二甲基吡喃并[4,3-c]吡唑-4(1H)-酮，以及不同数量的 N,N'-二取代 5-羟基-3-甲基-4-(3-甲基-1H-吡唑-5-基)-1H-吡唑。N-烷基肼和 4-氯-3-（1-氯乙烯基）-6-甲基-2H-吡喃-2-酮（“脱氢乙酰氯”）在没有副反应的情况下区域选择性地获得了相同的吡喃并吡唑啉酮，而 N-芳基肼得到了2-芳基-3,6-二甲基吡喃并[4,3-c]吡唑-4(2H)-酮。NMR NOE 方法，包括远程选择性异核 13C{1H}NOE 增强测量，允许明确区​​分 -4(1H)-ones 和 -4(2H)-ones。

  DOI：

  10.1246/bcsj.60.4425

文献信息

• SYNTHESIS AND UNAMBIGUOUS ASSIGNMENT OF STRUCTURE TO PYRANO[4,3-<i>c</i>]PYRAZOL-4(1<i>H</i>)-ONES AND -4(2<i>H</i>)-ONES
  作者：Albert Cantos、Pere De March、Marcial Moreno-Mañas、Anna Pla、Francisco Sanchez-Ferrando、Albert Virgili

  DOI：10.1246/cl.1986.295

  日期：1986.3.5

  A clean synthesis of pyranopyrazolones is described. The reactions of 4-chloro-3-(1-chlorovinyl)-6-methyl-2-pyrone with arylhydrazines give pyrano[4,3-c]pyrazol-4(2H)-ones as the only identified products. However, the isomeric pyrano [4,3-c]pyrazol-4(1H)-ones have been isolated when alkylhydrazines were used. Unambiguous assignment of structure could be achieved by homonuclear 1H1H} NOE determinations

  描述了吡喃并吡唑啉酮的清洁合成。4-氯-3-(1-氯乙烯基)-6-甲基-2-吡喃酮与芳基肼的反应产生吡喃并[4,3-c]吡唑-4(2H)-酮作为唯一确定的产物。然而，当使用烷基肼时，已分离出异构吡喃并 [4,3-c] 吡唑-4(1H)-酮。通过同核 1H1H} NOE 测定可以实现结构的明确分配。
• Design, synthesis, computational and biological evaluation of some new hydrazino derivatives of DHA and pyranopyrazoles
  作者：Ajay Kumar、Poonam Lohan、Deepak K. Aneja、Girish Kumar Gupta、Dhirender Kaushik、Om Prakash

  DOI：10.1016/j.ejmech.2012.01.042

  日期：2012.4

  Two series of compounds namely, 4-aryl/heteroaryl hydrazino-3-acetyl-6-methyl-2H-pyran-2-ones (4a-4j) and pyrano[4,3-c]pyrazoles (6a-6e and 6g) were synthesized starting from 3-acetyl-4-chloro-6-methyl-2H-pyran-2-one (2). Estimation of pharmacotherapeutic potential, possible molecular mechanism of action, toxic/side effects and interaction with drug-metabolizing enzymes were made for the synthesized compounds on the basis of prediction of activity spectra for substances (PASS) prediction results and their analysis by PharmaExpert software. COX inhibition predicted by PASS was confirmed by experimental evaluation and validated via docking studies. Out of all the compounds, compounds 4h, 4j, 6e, 6g exhibited good anti-inflammatory activity, whereas compounds 4b, 4c, 4h, 4i, 4j, 6b, 6e, 6g showed excellent analgesic activity compared with standard drug Diclofenac sodium. (C) 2012 Elsevier Masson SAS. All rights reserved.
• CANTOS, A.;DE, MARCH, P.;MORENO-MANAS, M.;PLA, A.;SANCHEZ-FERRANDO, F.;VI+, CHEM. LETT., 1986, N 3, 295-298
  作者：CANTOS, A.、DE, MARCH, P.、MORENO-MANAS, M.、PLA, A.、SANCHEZ-FERRANDO, F.、VI+

  DOI：——

  日期：——
• CANTOS, ALBERT;MARCH, PEDRO DE;MORENO-MANAS, MARCIAL;PLA, ANNA;SANCHEZ-FE+, BULL. CHEM. SOC. JAP., 60,(1987) N 12, # 4425-4431
  作者：CANTOS, ALBERT、MARCH, PEDRO DE、MORENO-MANAS, MARCIAL、PLA, ANNA、SANCHEZ-FE+

  DOI：——

  日期：——