Benzalacetophenon-p-tosylhydrazid | 25229-59-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Benzalacetophenon-p-tosylhydrazid
• 英文别名: N-(1,3-diphenylprop-2-enylideneamino)-4-methylbenzenesulfonamide
• CAS: 25229-59-8
• 化学式: C₂₂H₂₀N₂O₂S
• 分子量: 376.479
• InChiKey: HXNGKNHTSAKUIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzalacetophenon-p-tosylhydrazid 在 thallium(III) nitrate 作用下， 以 甲醇 为溶剂， 以81%的产率得到苯亚甲基苯乙酮
  参考文献：
  名称：

  用三硝酸铊 (TTN) 从甲苯磺酰腙中快速再生羰基化合物

  摘要：

  摘要 Tosylhydrazones 可以在温和的条件下用三硝酸铊 (TTN) 快速转化为相应的羰基化合物，产率很高。

  DOI：

  10.1080/00397919708004127
• 作为产物：
  描述：

  苯乙酮 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.08h， 生成 Benzalacetophenon-p-tosylhydrazid
  参考文献：
  名称：

  Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C–P(O) Cleavage

  摘要：

  A palladium-catalyzed two-component coupling of allenylphosphine oxides with conjugated N-tosylhydrazones is revealed. For the first time, the cleavage of a-allenylic aryl ether toward pyrazolemethylene-substituted phosphinyl allenes enabled facile synthesis of combined motifs with pyrazole and allene. Moreover, the obtained adducts could be easily transformed to potential bioactive multifunctionalized phosphinates via a novel alkenyl C-P(O) cleavage.

  DOI：

  10.1021/acs.orglett.7b00213

文献信息

• A facile and expeditious approach to substituted 1 H -pyrazoles catalyzed by iodine
  作者：Hailei Zhang、Qian Wei、Guodong Zhu、Jingping Qu、Baomin Wang

  DOI：10.1016/j.tetlet.2016.05.020

  日期：2016.6

  A facile and expeditious method for the synthesis of 1H-pyrazoles by the reaction of α,β-unsaturated aldehydes/ketones and sulfonyl hydrazide catalyzed by as low as 2 mol % I2 has been demonstrated. This synthetic system features simple operation and mild reaction conditions, and displays a broad functional group tolerance furnishing good to excellent yields.

  已经证明了通过低至2 mol％I 2催化α，β-不饱和醛/酮与磺酰肼反应合成1 H-吡唑的简便方法。该合成系统具有操作简单，反应条件温和的特点，并具有宽泛的官能团耐受性，可提供良好至优异的收率。
• Sunlight-promoted Direct Irradiation of <i>N</i> -centred Anion: The Photocatalyst-free Synthesis of Pyrazoles in Water
  作者：Te Zhang、Yunge Meng、Jinye Lu、Yuting Yang、Gong-Qiang Li、Chunyin Zhu

  DOI：10.1002/adsc.201701200

  日期：2018.8.17

  been developed for the synthesis of pyrazole. Based on the analysis of UV‐Vis absorption of the substrate, the reaction was designed to avoid the use of external photocatalysis and proceeds via direct irradiation of N‐centred anion by sunlight. The key features of this reaction include operational simplicity, readily available reagents, and amenability to gram‐scale synthesis.

  已经开发了一种通过日光介导的α，β-不饱和azo的环合反应的实用方法，用于合成吡唑。基于对底物的UV-Vis吸收的分析，该反应被设计为避免使用外部光催化，并通过阳光直接照射N中心阴离子进行反应。该反应的关键特征包括操作简便，易于获得的试剂以及对克级合成的适应性。
• Efficient one-pot synthesis of substituted pyrazoles
  作者：Meng Tang、Fu-Min Zhang

  DOI：10.1016/j.tet.2012.12.038

  日期：2013.2

  An efficient, one-pot synthesis of substituted pyrazoles from enones, hydrazides, and halides was developed. In comparison with the classical Knorr pyrazole synthesis, this methodology gave a different type of product (R3≥R5). A range of substituted pyrazoles were prepared in good to high yields with complete regioselectivity.

  从烯酮，酰肼和卤化物开始高效，一锅法合成取代的吡唑。与经典克诺尔吡唑合成相比，该方法给了一个不同类型的产品（R 3 ≥R 5）。制备了一系列具有良好收率和高收率并具有完全区域选择性的取代吡唑。
• Reactions of Tosylhydrazide Derivatives Having Olefinic Groups
  作者：Tadashi Sato、Itomi Homma

  DOI：10.1246/bcsj.44.1885

  日期：1971.7

  85% aqueous acetic acid, a smooth decomposition was induced and β-tosylketones (4) were obtained in fair yields. Tosylhydrazones, devoid of an olefinic group in the specified position, failed to undergo the present reaction. When allyl halides (17) were reacted with the anion of tosylhydrazide in DMSO, substitution occurred on the N-1 of tosylhydrazide, unlike as in the case of the reaction of chlorides

  当 α,β-不饱和酮甲苯磺酰腙 (5) 在 85% 乙酸水溶液中加热时, 诱导顺利分解, 并以相当的产率获得 β-甲苯磺酰酮 (4)。甲苯磺酰腙在指定位置没有烯基，不能进行本反应。当烯丙基卤化物 (17) 在 DMSO 中与甲苯磺酰肼的阴离子反应时，甲苯磺酰肼的 N-1 发生取代，这与氯化物与甲苯磺酰肼在吡啶中反应的情况不同，后者影响 N-2 的取代。在乙酸中加热时，这些 1-烯丙基糖基酰肼 (18) 以相当的产率提供烯烃 (19)，并具有完全的烯丙基重排。提出了 5→4 和 18→19 反应的协调循环机制。
• Electrocatalytic Synthesis of Substituted Pyrazoles <i>via</i> Hypervalent Iodine Mediated Intramolecular C−N Coupling
  作者：Stanislav A. Paveliev、Oleg O. Segida、Oleg V. Bityukov、Hai‐Tao Tang、Ying‐Ming Pan、Gennady I. Nikishin、Alexander O. Terent'ev

  DOI：10.1002/adsc.202200696

  日期：2022.11.22

  C(sp2)−H/N−H coupling of α,β-unsaturated hydrazones resulting in substituted pyrazoles has been discovered. The process is catalyzed by hypervalent iodine species generated in situ through anodic oxidation of aryl iodide in fluorinated alcohol media. The formation of hypervalent iodine compound and its key role in the construction of a new C−N bond was confirmed with CV and NMR experiments. A wide range

  已发现α、β-不饱和腙的电化学分子内交叉脱氢 C( sp 2 )-H/N-H 偶联，生成取代的吡唑。该过程由芳基碘在氟化醇介质中的阳极氧化原位产生的高价碘物质催化。CV 和 NMR 实验证实了高价碘化合物的形成及其在新 C-N 键构建中的关键作用。以 46% 至 88% 的产率获得了广泛的取代吡唑。