2-氰基-2-乙基丁酸乙酯 | 1619-56-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-氰基-2-乙基丁酸乙酯
• 中文别名: 乙基2-氰基-2-乙基丁酸酯
• 英文名称: ethyl 2-ethyl-2-cyanobutyrate
• 英文别名: 2,2-Diethyl-cyanessigsaeure-ethylester；Ethyl 2-cyano-2-ethylbutanoate
• CAS: 1619-56-3
• 化学式: C₉H₁₅NO₂
• mdl: MFCD00045613
• 分子量: 169.224
• InChiKey: MYPRYLUIKAKSET-UHFFFAOYSA-N

物化性质

• 沸点：
  298.52°C (rough estimate)
• 密度：
  1.0873 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2-氰基-2-乙基丁酸乙酯 在 sodium hydroxide 、 乙醚 、 五氯化磷 作用下， 生成 2,2-Diethyl-cyan-acetylchlorid
  参考文献：
  名称：

  Schroeter et al., Chemische Berichte, 1932, vol. 65, p. 432,441

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 diethyl-cyanoacetic ester 、 氨 作用下， 生成 2-氰基-2-乙基丁酸乙酯
  参考文献：
  名称：

  Hessler, American Chemical Journal, 1899, vol. 22, p. 171

  摘要：

  DOI：

文献信息

• Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: synthesis of alkyl aryl ketones
  作者：Md Yousuf、Tuluma Das、Susanta Adhikari

  DOI：10.1039/c5nj01597a

  日期：——

  containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester

  氰基乙酸乙酯/取代的氰基乙酸乙酯作为酰化剂，在三氟甲磺酸水溶液中有效地进行了钯催化的含各种官能团的芳基硼酸的酰化反应。首先通过将芳基硼酸加到氰基乙酸乙酯及其衍生物的腈基上，然后将所得的β-酮酯原位脱羧，从而以良好或优异的产率获得烷基芳基酮。
• First Cdc7 Kinase Inhibitors: Pyrrolopyridinones as Potent and Orally Active Antitumor Agents. 2. Lead Discovery
  作者：Maria Menichincheri、Alberto Bargiotti、Jens Berthelsen、Jay A. Bertrand、Roberto Bossi、Antonella Ciavolella、Alessandra Cirla、Cinzia Cristiani、Valter Croci、Roberto D’Alessio、Marina Fasolini、Francesco Fiorentini、Barbara Forte、Antonella Isacchi、Katia Martina、Antonio Molinari、Alessia Montagnoli、Paolo Orsini、Fabrizio Orzi、Enrico Pesenti、Daniele Pezzetta、Antonio Pillan、Italo Poggesi、Fulvia Roletto、Alessandra Scolaro、Marco Tatò、Marcellino Tibolla、Barbara Valsasina、Mario Varasi、Daniele Volpi、Corrado Santocanale、Ermes Vanotti

  DOI：10.1021/jm800977q

  日期：2009.1.22

  Furthermore, we also describe the discovery of 89S, [(S)-2-(2-aminopyrimidin-4-yl)-7-(2-fluoro-ethyl)-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one], as a potent ATP mimetic inhibitor of Cdc7. Compound 89S has a Ki value of 0.5 nM, inhibits cell proliferation of different tumor cell lines with an IC50 in the submicromolar range, and exhibits in vivo tumor growth inhibition of 68% in the A2780 xenograft model

  Cdc7激酶是细胞周期S期的关键调节因子，已知可促进真核生物中DNA复制起点的激活。Cdc7抑制作用可以以p53独立的方式导致肿瘤细胞死亡，这为开发用于治疗癌症的Cdc7抑制剂提供了理论依据。在本文中，我们总结了对Cdc7激酶具有抑制作用的2-杂芳基-吡咯并吡啶酮类化合物的构效关系研究。此外，我们还描述了89S，[（S）-2-（2-氨基嘧啶-4-基）-7-（2-氟乙基）-1,5,6,7-四氢吡咯并[3,2 - ç ]吡啶-4-酮]，作为具有Cdc7的有效ATP模拟物抑制剂。化合物89S的K i值为0.5 nM，在亚微摩尔范围内的IC 50抑制不同肿瘤细胞系的细胞增殖，并且在A2780异种移植模型中表现出68％的体内肿瘤生长抑制。
• Heilmittelchemische Studien in der heterocyclischen Reihe. 11. Mitteilung. 4,4-Disubstituierte Derivate der Pyrazolreihe
  作者：J. Druey、P. Schmidt

  DOI：10.1002/hlca.19540370629

  日期：——

  By alkylation of the pyrazole derivatives obtained from disubstituted cyano-acetic acid esters and hydrazine (formula 1) a series of 1-alkyl-3-amino-4,4-disubstituted-5-oxo-pyrazolines (7) was obtained. These were further alkylated to 1,2-dialkyl derivatives (8). From the compounds 1 the 5-halogenated iminopyrazolines 9 were obtained with POCl3 or PBr5. The 4-methyl-4-n-butyl-5-bromo derivative of

  通过对由二取代的氰基乙酸酯和肼获得的吡唑衍生物进行烷基化（式1），获得了一系列的1-烷基-3-氨基-4,4-二取代的5-氧代-吡唑啉（7）。将它们进一步烷基化为1，2-二烷基衍生物（8）。从化合物1获得带有POCl 3或PBr 5的5-卤代亚氨基吡唑啉9。该系列的4-甲基-4-正丁基-5-溴衍生物具有重要的镇静作用。与Pd / H 2催化脱卤得到3-亚氨基-4,4-二烷基吡唑啉10。研究了不同类型化合物的酰化作用。
• The design and synthesis of potent cyclic peptide VCAM–VLA-4 antagonists incorporating an achiral Asp-Pro mimetic
  作者：Nader Fotouhi、Pramod Joshi、David Fry、Charles Cook、Jefferson W Tilley、Gerry Kaplan、Angela Hanglow、Karen Rowan、Virginia Schwinge、Barry Wolitzky

  DOI：10.1016/s0960-894x(00)00174-8

  日期：2000.6

  The Asp-Pro sequence of the cyclic peptide Ac-HN-Tyr-Cys*-Asp-Pro-Cys*-OH (1) could be replaced with the achiral dipeptide mimetic 1-(2-aminoethyl)cyclpentylcarboxylic acid with retention of potent inhibition of the VCAM-VLA-4 interaction.

  环状肽Ac-HN-Tyr-Cys * -Asp-Pro-Cys * -OH（1）的Asp-Pro序列可被非手性二肽模拟1-（2-氨基乙基）环戊基羧酸取代抑制VCAM-VLA-4相互作用。
• Acyl compounds
  申请人：Ciba-Geigy Corp

  公开号：US05399578A1

  公开（公告）日：1995-03-21

  Compounds of the formula ##STR1## in which R.sub.1 is an aliphatic hydrocarbon radical which is unsubstituted or substituted by halogen or hydroxyl, or a cycloaliphatic or araliphatic hydrocarbon radical; X.sub.1 is CO, SO.sub.2, or --O--C(.dbd.O)-- with the carbon atom of the carbonyl group being attached to the nitrogen atom shown in formula I; X.sub.2 is a divalent aliphatic hydrocarbon radical which is unsubstituted or substituted by hydroxyl, carboxyl, amino, guanidino or a cycloaliphatic or aromatic radical, or is a divalent cycloaliphatic hydrocarbon radical, it being possible for a carbon atom of the aliphatic hydrocarbon radical to be additionally bridged by a divalent aliphatic hydrocarbon radical; R.sub.2 is carboxyl which, if desired, is esterified or amidated, substituted or unsubstituted amino, formyl which, if desired, is acetalized, 1H-tetrazol-5-yl, pyridyl, hydroxyl which, if desired, is etherified, S(O).sub.m --R where m is 0, 1 or 2 and R is hydrogen or an aliphatic hydrocarbon radical, alkanoyl, unsubstituted or N-substituted sulfamoyl or PO.sub.n H.sub.2 where n is 2 or 3; X.sub.3 is a divalent aliphatic hydrocarbon; R.sub.3 is carboxyl, 5-tetrazolyl, SO.sub.3 H, PO.sub.2 H.sub.2, PO.sub.3 H.sub.2 or haloalkylsulfamoyl; and the rings A and B independently of one another are substituted or unsubstituted; in free form or in salt form, can be prepared in a manner known per se and can be used, for example, as medicament active ingredients.

  式为##STR1##的化合物，其中R.sub.1是未取代或取代为卤素或羟基的脂肪烃基，或者是环脂烃或芳基脂肪烃基；X.sub.1是CO、SO.sub.2或--O--C(.dbd.O)--，其中羰基的碳原子连接到式I中显示的氮原子；X.sub.2是未取代或取代为羟基、羧基、氨基、胍基或环脂烃或芳香基的二价脂肪烃基，或者是二价环脂烃脂肪烃基，脂肪烃基的碳原子还可以通过另一个二价脂肪烃基进行桥接；R.sub.2是羧基，如果需要，可以酯化或酰胺化，取代或未取代的氨基，甲酰基，如果需要，可以缩醛化，1H-四唑-5-基，吡啶基，羟基，如果需要，可以醚化，S(O).sub.m --R，其中m为0、1或2，R为氢或脂肪烃基，烷酰基，未取代或N-取代的磺酰胺基或PO.sub.n H.sub.2，其中n为2或3；X.sub.3是二价脂肪烃基；R.sub.3是羧基，5-四唑基，SO.sub.3 H，PO.sub.2 H.sub.2，PO.sub.3 H.sub.2或卤代烷基磺酰胺基；环A和B彼此独立地被取代或未取代；以自由形式或盐形式，可以按已知方法制备，并可用作药物活性成分。

表征谱图