1-苄基-3-甲基-2-吡唑-5-酮 | 946-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 1-苄基-3-甲基-2-吡唑-5-酮
• 英文名称: 1-benzyl-3-methyl-3-pyrazolin-5-one
• 英文别名: 1-benzyl-3-methyl-1H-pyrazol-5(4H)-one；2-Pyrazolin-5-one, 1-benzyl-3-methyl-；2-benzyl-5-methyl-4H-pyrazol-3-one
• CAS: 946-23-6
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00461211
• 分子量: 188.229
• InChiKey: MEDQPHZEAUFCTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-苄基-3-甲基-2-吡唑-5-酮 在 亚硝酸 作用下， 以95%的产率得到1-benzyl-3-methyl-4-hydroximino-5-pyrazolone
  参考文献：
  名称：

  Lanovaya, G. A.; Mashikhina, A. S.; Fedorova, V. A., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 9, p. 1773 - 1776

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 苄基肼 以 甲苯 为溶剂， 反应 17.0h， 生成 1-苄基-3-甲基-2-吡唑-5-酮
  参考文献：
  名称：

  吡唑啉酮的无金属直接C–H硫代和硫氰化

  摘要：

  在温和的条件下，分别成功开发了吡唑啉酮与二硫化物和硫氰酸盐的无金属直接硫醇化和硫氰化物。

  DOI：

  10.1002/ejoc.201901770

文献信息

• Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole‐4,5‐Diones and Indoline‐2,3‐Diones
  作者：Rong‐Hui Wang、Ya‐Ling Li、Hong‐Jiao He、You‐Cai Xiao、Fen‐Er Chen

  DOI：10.1002/chem.202005081

  日期：2021.3

  The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin‐4,5‐diones and isatins have been developed. In the presence of morpholine‐containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes

  已经开发了对环二酮（包括吡唑啉-4,5-二酮和靛红）的催化对映选择性二有机锌。在含有吗啉的手性氨基醇配体存在的情况下，相应的手性环状叔醇以良好至极佳的收率（高达97％）和对映选择性（高达95％ee）生产。该方案的显着特征包括温和的反应条件，无路易斯酸添加剂和宽泛的官能团耐受性。
• Potassium iodide promoted thiolation of pyrazolones and benzofurans using aryl sulfonyl chlorides as sulfenylation reagents
  作者：Xia Zhao、Xiaoyu Lu、Aoqi Wei、Xiaoliang Jia、Jun Chen、Kui Lu

  DOI：10.1016/j.tetlet.2016.10.053

  日期：2016.11

  thioethers as well as 2-aryl and 3-aryl benzofuran thioethers by employing aryl sulfonyl chlorides as sulfenylation reagents in the presence of triphenylphosphine was developed. Potassium iodide was found to facilitate the transformation for the first time by generating more reactive sulfenyl iodide in situ from sulfenyl chloride.

  开发了一种有效的，无过渡金属的方法，该方法通过在三苯基膦存在下使用芳基磺酰氯作为亚磺酰基化试剂来合成吡唑啉酮硫醚以及2-芳基和3-芳基苯并呋喃硫醚。发现碘化钾通过从亚磺酰氯原位产生更多反应性的亚硫基碘化物，首次促进了转化。
• p-Toluenesulphonic acid-promoted, I₂-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides
  作者：Xia Zhao、Lipeng Zhang、Tianjiao Li、Guiyan Liu、Haomeng Wang、Kui Lu

  DOI：10.1039/c4cc05237d

  日期：——

  Aryl pyrazolone thioethers were synthesized via the I2-catalysed cross-coupling of pyrazolones with aryl sulphonyl hydrazides in the presence of p-toluenesulphonic acid, which has been proposed to promote the reaction by facilitating the decomposition of sulphonyl hydrazides.

  芳基吡唑酮硫醚通过I2催化的吡唑酮与芳基磺酰肼在邻甲苯磺酸存在下的交叉耦合反应合成，该工艺已提议通过促进磺酰肼的分解来促进反应。
• Fused ring compound
  申请人：Tawaraishi Taisuke

  公开号：US20080194617A1

  公开（公告）日：2008-08-14

  The present invention provides an agent for the prophylaxis or treatment of diabetes, which has a superior hypoglycemic action, and is associated with a fewer side effects such as body weight gain and the like. The present invention relates an agent for the prophylaxis or treatment of diabetes, which comprises a compound represented by wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof.

  本发明提供了一种用于预防或治疗糖尿病的药剂，具有优越的降血糖作用，并且与较少的副作用（如体重增加等）相关。本发明涉及一种用于预防或治疗糖尿病的药剂，包括由下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。
• Tandem stereoselective synthesis of new trifluoromethylated pyranopyrazoles
  作者：Jian Wang、Guan-Bo Huang、Li-Jun Yang、Feng Li、Jing Nie、Jun-An Ma

  DOI：10.1016/j.jfluchem.2014.10.008

  日期：2015.3

  trifluoromethyl ketones is described. The notable features of this tandem process are its operational simplicity, easily accessible starting materials, and mild reaction conditions. The corresponding trifluoromethylated pyranopyrazoles were obtained in excellent yields (85–99%) with good to excellent diastereoselectivities (6:1–30:1). In addition, the stereochemical assignment of the major isomer by X-ray crystallographic

  描述了吡唑啉酮与α，β-不饱和三氟甲基酮的有效串联迈克尔加成/芳构化/环化反应。该串联方法的显着特征是操作简单，易于获得的起始原料以及温和的反应条件。相应的三氟甲基化吡喃并吡咯类化合物的收率很高（85–99％），非对映选择性很好（6：1–30：1）。另外，通过X射线晶体学分析对主要异构体的立体化学分配表明主要形成反式产物。