methyl benzoyl formate phenylhydrazone | 23102-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl benzoyl formate phenylhydrazone
• 英文别名: methyl 2-(phenylhydrazono)-2-phenyl-acetate；phenyl-phenylhydrazono-acetic acid methyl ester；Phenyl-phenylhydrazono-essigsaeure-methylester；Methyl 2-phenyl-2-phenylhydrazonoacetate；methyl 2-phenyl-2-(phenylhydrazinylidene)acetate
• CAS: 23102-13-8
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: PBPDDJFMXWRDEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  374.2±25.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl benzoyl formate phenylhydrazone 在 palladium on activated charcoal 吡啶 、 甲酸铵 作用下， 以 乙二醇 为溶剂， 反应 0.07h， 生成 2-乙酰氨基-2-苯基乙酸甲酯
  参考文献：
  名称：

  Microwave-Assisted Rapid and Simplified Hydrogenation^1,

  摘要：

  Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 degrees C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 degrees C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of beta-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters, Cleavage of the beta-lactam ring by hydrogenolysis of the N-C-4 bond of 4-aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

  DOI：

  10.1021/jo981516s
• 作为产物：
  描述：

  DL-扁桃酸甲酯 在 lead(IV) acetate 、 苯 作用下， 生成 methyl benzoyl formate phenylhydrazone
  参考文献：
  名称：

  A New Method of Preparing Phenylglyoxylic Acid and its Methyl Ester

  摘要：

  DOI：

  10.1021/ja01225a022

文献信息

• Synthesis of 1<i>H</i>-indazoles by an electrochemical radical C_sp²–H/N–H cyclization of arylhydrazones
  作者：Hao Wan、Dongting Li、Huadan Xia、Liwen Yang、Hesham Alhumade、Hong Yi、Aiwen Lei

  DOI：10.1039/d1cc04656j

  日期：——

  bond-forming reactions to N-heterocyclic frameworks has been a long-standing interest in organic synthesis. In this work, we develop an electrochemical radical Csp2–H/N–H cyclization of arylhydrazones to 1H-indazoles. The electrochemical anodic oxidation approach was adopted to synthesize a variety of 1H-indazole derivatives in moderate to good yields. HFIP was not only employed as a solvent or the proton donor

  对 N-杂环骨架进行高效且可持续的 C-N 键形成反应一直是有机合成领域的长期兴趣。在这项工作中，我们开发了芳基腙到 1 H-吲唑的电化学自由基 C sp 2 -H/N-H 环化。采用电化学阳极氧化方法合成了多种1 H-吲唑衍生物，产率中等至较好。HFIP不仅用作溶剂或质子供体，而且可以促进N自由基的形成。这种合成方法操作简单，较便宜的电极适用于这种化学。
• Reaction of ketene silyl acetals with diazonium salts: a novel α-amino acid ester synthesis
  作者：Toshiyasu Sakakura、Masato Tanaka

  DOI：10.1039/c39850001309

  日期：——

  The reaction of ketene silyl acetals with arenediazonium tetrafluoroborate gave α-hydrazono and α-azo esters, which were easily hydrogenated to α-amino esters.

  乙烯酮甲硅烷基缩醛与四氟硼酸壬二唑鎓的反应得到α-肼基和α-偶氮酯，它们很容易被氢化成α-氨基酯。
• Facile Access to 1<i>H</i>-Indazoles through Iodobenzene-Catalyzed C-H Amination under Mild, Transition-Metal-Free Conditions
  作者：Mitsuhiro Kashiwa、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1002/ejoc.201402488

  日期：2014.8

  1H-indazole and derivatives was accomplished on the basis of the iodobenzene-catalyzed intramolecular C–H amination of hydrazones under mild conditions. Reactions of hydrazones derived from ketones and hydrazines with a catalytic amount of iodobenzene in the presence of Oxone as an oxidant in trifluoroacetic acid took place to afford 1H-indazoles in moderate to good yields. A plausible reaction mechanism

  N-芳基取代的1H-吲唑及其衍生物的无过渡金属和无卤素合成是在碘苯催化的腙分子内C-H胺化反应的基础上在温和条件下完成的。由酮和肼衍生的腙与催化量的碘苯在 Oxone 作为氧化剂的三氟乙酸中发生反应，以中等至良好的产率得到 1H-吲唑。在对照实验的基础上描述了一个合理的反应机理。
• Process for preparing .alpha.-substituted carbonyl compound
  申请人：Agency of Industrial Science and Technology

  公开号：US04908451A1

  公开（公告）日：1990-03-13

  A process is disclosed for the preparation of .alpha.-substituted carbonyl compounds, wherein .alpha.-substituted ketone is prepared by the following reaction: ##STR1## .alpha.-azo ester is prepared by the following reaction: ##STR2## and .alpha.-hydrozono ester is prepared by the following reaction: ##STR3## wherein the .alpha.-azo ester and .alpha.-hydrazono ester obtained by the above reactions include novel compounds, which are also disclosed.

  本发明揭示了一种制备α-取代羰基化合物的方法，其中通过以下反应制备α-取代酮：##STR1## 通过以下反应制备α-偶氮酯：##STR2## 通过以下反应制备α-肼酰基酯：##STR3## 通过上述反应获得的α-偶氮酯和α-肼酰基酯包括新化合物，也在本发明中揭示。
• Process for the preparation of .alpha.-aryl and .alpha.-heteroaryl
  申请人：Agency of Industrial Science & Technology

  公开号：US04772714A1

  公开（公告）日：1988-09-20

  Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##

  公开了一种制备α-芳基和α-杂环基酮的过程，该酮可用作合成各种医药和农业化学品的中间体，该过程根据以下反应方程式进行操作：##STR1##