ethyl (ethoxymethylene)cyanoacetate | 72459-84-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (ethoxymethylene)cyanoacetate
• 英文别名: ethyl (ethoxymethylene)cyanacetate；ethyl ethoxymethylene cyanoacetate；ethyl ethoxymethylene-cyanoacetate；ethyl(ethoxymethylene)cyanoacetate；ethyl ethoxymethylenecyanoacetate；ethyl ethoxymethylcyanoacetate；Ethyl 2-cyano-3-ethoxypropanoate
• CAS: 72459-84-8
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: XIAJZVAZEWWSDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C
• 沸点：
  289.2±20.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (ethoxymethylene)cyanoacetate 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 potassium phosphate 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 96.0h， 生成 5-[acetyl-(4-iodo-phenyl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Application of Ullmann and Ullmann–Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation

  摘要：

  Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT, receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.056

文献信息

• Alkylamino-substituted bicyclic nitrogen heterocycles
  申请人：Syntex (U.S.A.) LLC

  公开号：US06642241B1

  公开（公告）日：2003-11-04

  Alkylamino-substituted dihydropyrimido[4,5-d]pyrimidinone derivatives are provided which are useful as inhibitors of p38, along with a process for their manufacture and pharmaceutical preparations containing them.

  提供了烷基氨基取代的二氢嘧啶[4,5-d]嘧啶酮衍生物，这些衍生物可用作p38的抑制剂，以及它们的制备过程和含有它们的药物制剂。
• Synthesis and Reactions of Novel Pyrimido[4,5-c]pyridazine and s-Triazolo[3?,4?:2,3]pyrimido[4,5-c]pyridazine Derivatives
  作者：Maisa I. Abdel Moneam

  DOI：10.1007/s00706-003-0078-1

  日期：2004.1.1

  reaction of 3-chloro-5,6-diphenylpyridazine-4-carbonitrile with potassium thiocyanate gave the corresponding isothiocyanate derivative. This was reacted with aromatic amines in ethanol to afford pyrimido[4,5- c ]pyridazine derivatives. The reaction of the latter compounds with hydrazine hydrate led to the formation of 6-hydrazino derivatives. One hydrazino compound was reacted with a variety of reagents

  3-氯-5，6-二苯基哒嗪-4-腈与硫氰酸钾的反应得到相应的异硫氰酸酯衍生物。使它与芳族胺在乙醇中反应，得到嘧啶并[4,5- c ]哒嗪衍生物。后者化合物与水合肼的反应导致6-肼基衍生物的形成。一种肼化合物用多种试剂以产生其它新pyrimidopyridazines以及许多反应 小号 -三唑并衍生物。
• [EN] ANDROGEN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DES ANDROGÈNES
  申请人：ALPINE ANDROSCIENCES INC

  公开号：WO2019152731A1

  公开（公告）日：2019-08-08

  Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

  描述了抑制雄激素受体的化合物、包含一种或多种这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• SYNTHESIS, REACTIONS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 1,3,4- OXADIAZOLES, 1,2,4-TRIAZOLES AND 1,3,4-THIADIAZINES DERIVED FROM PYRAZOLE
  作者：A. A. Farghaly、P. Vanelle、H. S. El-Kashef

  DOI：10.1515/hc.2005.11.3-4.255

  日期：2005.1

  pyrrol-1-yl ester 2 via the interaction with dimethoxytetrahydrofuran (DMTHF) in acidic medium.' This latter pyrrolyl ester gave the hydrazide 3 upon treatment with hydrazine hydrate. In the light of the antibacterial and antifungal activities of the arylidene hydrazides 4,' a series of arylidene derivatives 5a-l of the hydrazide 3 was prepared by the reaction of the latter compound with different aldehydes

  使用乙基 5-氨基-1-苯基///-吡唑-3-制备含有吡唑基部分 7-14 的新型 1,3,4-恶二唑、1,2,4-三唑和 1,3,4-噻二嗪羧酸盐 1 作为起始原料。筛选新合成的化合物的体外抗菌和抗真菌活性。引言 长期以来，人们都知道 1,2,4-三唑具有多种生物活性，例如抗病毒、抗菌、抗炎、抗惊厥和抗真菌活性。另一方面，据报道，1,3,4-恶二唑具有抗糖尿病、抗炎和镇痛活性。”“还有一些亚芳基酰肼具有抗菌活性。” 牢记上述结果，并继续我们对合成具有潜在生物活性的吡唑杂环的兴趣，'” 我们在此报告了从吡唑衍生的一些新的恶二唑、三唑和噻二嗪的合成。结果与讨论 通过与二甲氧基四氢呋喃 (DMTHF) 的相互作用，容易获得的 5-氨基-1-苯基-7//-吡唑-3-羧酸乙酯 1 的氨基很容易转化为相应的吡咯-1-基酯 2在酸性介质中。后一种吡咯酯在用水合肼处理后得到酰肼3。鉴于亚芳基酰肼4'的抗
• Novel Pyrazolo[3,4-<i>d</i>]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation
  作者：Xiang Cheng、Wei Wang、Yunxiao Wang、Dongguo Xia、Fang Yin、Qiaoyun Liu、Huisheng Luo、Meng Li、Chengqi Zhang、Haiqun Cao、Xianhai Lv

  DOI：10.1021/acs.jafc.1c02454

  日期：2021.9.29

  seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound

  植物病原真菌严重威胁农业生产。迫切需要开发低毒高效的新型杀菌剂。在本研究中，我们设计并合成了 44 种 pyrazolo[3,4- d ]pyrimidin-4-one 衍生物，并评估了它们的杀菌活性。生物测定数据表明，大多数目标化合物具有中到高的体外抗真菌活性。特别是化合物g22对核盘菌表现出显着的抗真菌活性，EC 50值为1.25 mg/L，接近商业杀菌剂啶酰菌胺（EC 50 = 0.96 mg/L）和氟吡菌酰胺（EC 50= 1.91 毫克/升）。此外，化合物g22在体内 24 小时 (95.23%) 和 48 小时 (93.78%)具有显着的抗核盘菌保护活性，与阳性对照啶酰菌胺(24 小时 (96.63%)；48 小时 (93.23%))相当。随后的研究表明，化合物g22可能通过影响菌丝体的形态、破坏细胞膜完整性和增加细胞膜通透性来阻碍核盘菌的生长和繁殖。此外，化合物g22的施用并