2-butyl-5-chloro-1,2-dihydro-3H-indazol-3-one | 89438-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 2-butyl-5-chloro-1,2-dihydro-3H-indazol-3-one
• 英文别名: 2-butyl-5-chloro-1H-indazol-3-one
• CAS: 89438-57-3
• 化学式: C₁₁H₁₃ClN₂O
• 分子量: 224.69
• InChiKey: CKXXPKIAURTZLX-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±44.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-3-氧代-2H-吲唑-1-羧酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 2-butyl-5-chloro-1,2-dihydro-3H-indazol-3-one
  参考文献：
  名称：

  Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs

  摘要：

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.

  DOI：

  10.1021/jm00372a011

文献信息

• Photochemical Preparation of 1,2-Dihydro-3<i>H</i>-indazol-3-ones in Aqueous Solvent at Room Temperature
  作者：Jie S. Zhu、Niklas Kraemer、Clarabella J. Li、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/acs.joc.8b02356

  日期：2018.12.21

  involve its isolation via chromatography and/or formation under harsh conditions. Herein, this intermediate was photochemically generated in situ from o-nitrobenzyl alcohols in a mild, efficient manner for the construction of 1,2-dihydro-3 H-indazol-3-ones using an aqueous solvent at room temperature. This convenient reaction offers several advantages over reported methods. The commercially available photoreactor

  邻硝基苯甲醛是一种反应性中间体，可用于合成氮杂环。以前使用邻亚硝基苯甲醛的策略涉及通过色谱分离和/或在苛刻条件下形成。在此，该中间体以温和，有效的方式从邻硝基苄基醇原位光化学生成，用于在室温下使用水性溶剂构建1,2-二氢-3 H-吲唑-3-酮。与报道的方法相比，这种方便的反应具有多个优点。市售的光反应器使用3×18 W灯泡，可在365 nm以上发出宽广的发射光。
• N–N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
  作者：Jie S. Zhu、Niklas Kraemer、Marina E. Shatskikh、Clarabella J. Li、Jung-Ho Son、Makhluf J. Haddadin、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1021/acs.orglett.8b01655

  日期：2018.8.17

  A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol -> o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation.
• Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs
  作者：Steven D. Wyrick、P. Josee Voorstad、George Cocolas、Iris H. Hall

  DOI：10.1021/jm00372a011

  日期：1984.6

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.