ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate | 545445-35-0

• 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: ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate
• 英文别名: ethyl glyoxylate 4-methoxyphenylhydrazone；ethyl glyoxalate p-methoxyphenylhydrazone；[(4-Methoxyphenyl)hydrazono]acetic acid ethyl ester；ethyl 2-[(4-methoxyphenyl)hydrazinylidene]acetate
• CAS: 545445-35-0
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: PEMOHLVNDVUGTF-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  326.5±44.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate 在 重水 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Vinylogous Reactivity of Enol Diazoacetates with Donor–Acceptor Substituted Hydrazones. Synthesis of Substituted Pyrazole Derivatives

  摘要：

  A regiospecific synthesis of multifunctional pyrazoles has been developed from a cascade process triggered by Rh(II)-catalyzed dinitrogen extrusion from enol diazoacetates with vinylogous nucleophilic addition followed by Lewis acid catalyzed cyclization and aromatization.

  DOI：

  10.1021/jo302696y
• 作为产物：
  描述：

  ethyl 3-hydroxy-2-(p-methoxyphenylhydrazono)butyrate 反应 0.5h， 生成 ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate 、 ethyl 6-[ethoxycarbonyl-(p-methoxyphenylhydrazono)-methyl]-4-methyl-1-(p-methoxyphenyl)-1,4,5,6-tetrahydropyridazine-3-carboxylate
  参考文献：
  名称：

  3-羟基-2-芳基肼基链烷酸衍生物的热解

  摘要：

  在各种反应条件下，包括热解，在Mitsunobu条件下脱水或用乙酸酐或乙酸，从容易获得的3-羟基-2-芳基肼基丙酸酯中获得1,2-Diaza-1,3-丁二烯。根据他们的合成方法，使这些1,2-二氮杂1,3-丁二烯进行后续反应，得到有趣的产物，并在适当的二烯亲和剂存在下得到相应的环加成产物。同样，在尝试使3-羟基-2-芳基肼基丁酸酸酯脱水的过程中，发现了一种新的吡唑-3-羧酸衍生物的方法。

  DOI：

  10.1016/j.tet.2010.11.074

文献信息

• Metal-Free Tandem Oxidative Cyclization for the Synthesis of 1,2-Dihydropyridazines and Pyrazoles
  作者：Dongping Cheng、Yinqiang Shen、Ziliang Wu、Xiaoliang Xu、Jizhong Yan

  DOI：10.1021/acs.joc.1c00020

  日期：2021.7.2

  disclosed to generate appealing β,γ-unsaturated hydrazones, which further undergo 5-exo-trig or 6-endo-trig cascade cyclization to give the respective 1,2-dihydropyridazines or pyrazoles selectively under metal-free conditions. The mechanisms of the coupling and subsequent cyclization are proposed.

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 介导下，腙和 1,3-二芳基丙烯的新型氧化偶联已被公开，可生成有吸引力的 β,γ-不饱和腙，这进一步在无金属条件下进行5- exo -trig或6- end -trig级联环化，选择性地生成各自的1,2-二氢哒嗪或吡唑。提出了偶联和随后环化的机制。
• N-Heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals with hydrazones: highly enantioselective synthesis of dihydropyridazones
  作者：Chun-Lin Zhang、Dong-Ling Wang、Kun-Quan Chen、Song Ye

  DOI：10.1039/c5ob01748c

  日期：——

  The N-heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals and hydrazones is developed to give the corresponding chiral 4,5-dihydropyridazones in good yields with excellent enantioselectivities.

  N-杂环卡宾催化的溴代烯和als的[3 + 3]环缩合反应得到良好的收率，具有出色的对映选择性，从而得到相应的手性4,5-二氢吡啶并酮。
• N-Heterocyclic Carbene-Catalyzed Oxidative Annulations of α,β-Unsaturated Aldehydes with Hydrazones: Selective Synthesis of Optically Active 4,5-Dihydropyridazin-3-ones and Pyridazin-3-ones
  作者：Jian-Hui Mao、Zi-Tian Wang、Zhan-Yong Wang、Ying Cheng

  DOI：10.1021/acs.joc.5b00784

  日期：2015.6.19

  A novel and efficient method for the highly enantioselective synthesis of chiral 4,5-dihydropyridazin-3-one derivatives has been developed based on the chiral N-heterocyclic carbene-catalyzed oxidative annulation between α,β-unsaturated aldehydes and hydrazones. Meanwhile, the selective synthesis of either 4,5-dihydropyridazin-3-ones or pyridazin-3-one derivatives from the same reactants has been achieved

  基于α，β-不饱和醛与的手性N-杂环卡宾催化的氧化环合反应，开发了一种新型的高效手性4,5-二氢哒嗪-3-酮衍生物的高对映选择性合成方法。同时，通过简单地改变催化和反应条件就可以从相同的反应物中选择性地合成4，5-二氢哒嗪-3-酮或哒嗪-3-酮衍生物。
• Silver(I)-Catalyzed Tandem Sigamatropic Rearrangement/1,3-H Shift/6π Aza-electrocyclization of <i>N</i>-Propargylic Hydrazones: A Mild Synthetic Route to 1,6-Dihydropyridazines
  作者：Zong-Cang Ding、Lu-Chuan Ju、Ying Yang、Xiao-Ming An、Yun-Bing Zhou、Ren-Hao Li、Hai-Tao Tang、Cheng-Ke Ding、Zhuang-Ping Zhan

  DOI：10.1021/acs.joc.6b00428

  日期：2016.5.6

  A highly efficient AgOTf catalyzed [3,3] sigmatropic rearrangement/1,3-H shift/6π aza-electrocyclization cascade reaction of N-propargylic hydrazones has been developed. This method provides a new mild synthetic route to various polysubstituted 1,6-dihydropyridazines including the 3-CF3-substituted ones with high selectivity.

  A高效催化的AgOTf [3,3]σ重排/ 1,3--H移位/的6π氮杂electrocyclization级联反应Ñ -propargylic腙已经研制成功。该方法提供了一种新的温和的合成路线，以高选择性合成各种多取代的1,6-二氢哒嗪，包括3-CF 3-取代的。
• Palladium and Copper Cocatalyzed Intermolecular Cyclization Reaction: Synthesis of 5-Aminopyrazole Derivatives
  作者：Chaowei Ma、Ping Wen、Jihui Li、Xu Han、Zhaoyang Wu、Guosheng Huang

  DOI：10.1002/adsc.201500767

  日期：2016.3.31

  A novel and efficient palladium and copper co‐catalyzed intermolecular cyclization of acetonitriles with hydrazones has been developed for the synthesis of 5‐aminopyrazoles through CC and CN bond formation. The reaction has the advantages of easily available starting materials, simple manipulation and mild reaction conditions. The reaction involving various substituted acetonitriles and hydrazones

  已开发出一种新颖且有效的钯和铜与共催化的乙腈分子间环化反应，用于通过C CC和CN键的形成合成5-氨基吡唑。该反应具有容易获得的起始原料，简单的操作和温和的反应条件的优点。涉及各种取代乙腈和的反应进行得很顺利，并且以高收率合成了5-氨基吡唑。与脂族和杂芳族底物相反，芳族底物倾向于具有更高的反应性。