2-(N-Methylanilino)-acrylonitril | 69567-06-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N-Methylanilino)-acrylonitril
• 英文别名: 2-(N-Methylanilino)-propennitril；2-(N-Methylanilino)-acrylnitril；2-[Methyl(phenyl)amino]prop-2-enenitrile；2-(N-methylanilino)prop-2-enenitrile
• CAS: 69567-06-2
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: WJFCMLXARVNIJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(N-Methylanilino)-acrylonitril 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 45.5h， 生成 (Z)-2-(N-Methylanilino)-2-pentennitril
  参考文献：
  名称：

  Pyrrol-Anellierung von Ketonen durch Addition deprotonierter Imine an 2,-(N-Methylanilino)-acrylonitrile

  摘要：

  DOI：

  10.1055/s-1984-30914
• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 2-(N-Methylanilino)-acrylonitril
  参考文献：
  名称：

  2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions

  摘要：

  2-(N-Methylanilino) -2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide. Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates. Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by Cul or Lewis acids to give varied alpha-amino nitriles. The 4-oxo-2-amino nitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung. When 1 was treated with tributylstannane, the corresponding amino nitrile alpha-radical was formed and the self-coupling product was isolated.

  DOI：

  10.1039/p19940002217

文献信息

• 1,5-Dicarbonyl-Verbindungen durch Michael-Addition deprotonierter Enamine und Allylamine an 2-(<i>N</i>-Methylanilino)-acrylnitril
  作者：Hubertus Ahlbrecht、Manfred Dietz、Lothar Weber

  DOI：10.1055/s-1987-27904

  日期：——

  1,5-Dicarbonyl Compounds via Michael-Addition of Deprotonated Enamines and Allylamines to 2-(N-Methylanilino) acrylonitrile A new method for the synthesis of the title compounds by a onepot, three component, coupling reaction is described. Is consists of the reaction of a homoenolate anion and an enol cation equivalent with subsequent alkylation of an acyl-anion equivalent. Hence the methodology of Umpolung is used in a threefold manner within the reaction sequence.

  经由迈克尔加成反应合成1,5-二羰基化合物：通过去质子化的烯胺和烯丙胺对2-(N-甲基苯胺基)丙烯腈的反应。描述了一种新的合成标题化合物的一锅法、三组分偶联反应方法。该方法包括一个同烯醇盐负离子和一个烯醇正离子等价物的反应，随后是酰基负离子等价物的烷基化反应。因此，在反应序列中，极性反转策略被以三种不同的方式应用。
• Efficient regioselective synthesis of 4- and 5-substituted isoxazoles under thermal and microwave conditions
  作者：Jamal Lasri、Suman Mukhopadhyay、M. Adflia Januário Charmier、M. Adflia Januário Charmier

  DOI：10.1002/jhet.5570450521

  日期：2008.9

  The [2+3] cycloaddition reaction between nitrile oxides 2 and the captodative olefins 1 or the methyl crotonate derivatives 4 is regioselective and leads to the formation of the 5-substituted amino-isoxazole 3 or the 4-substituted methoxycarbonyl-isoxazole 5 derivatives, respectively. All these reactions are greatly accelerated by microwave irradiation without changing their regioselectivity with respect

  腈氧化物2与俘获性烯烃1或巴豆酸甲酯衍生物4之间的[2 + 3]环加成反应是区域选择性的，并导致形成5-取代的氨基-异恶唑3或4-取代的甲氧基羰基-异恶唑5的衍生物，分别。微波辐照极大地加速了所有这些反应，而没有改变它们相对于热条件的区域选择性。
• 1,4-Ketoaldehyde durch Michael-Addition deprotonierter Aldimine an 2-(<i>N</i>-Methylanilino)-acrylonitril
  作者：Hubertus Ahlbrecht、Axel Von Daacke

  DOI：10.1055/s-1987-27829

  日期：——

  1,4-Ketoaldehydes via Michael-Addition of deprotonated Aldimines to 2-(N-Methylanilino)-acrylonitrile A new method for the synthesis of the title compounds by a one-pot three component coupling reaction is described. It consists of the reaction of an enolateanion- and an enolcation-equivalent with subsequent alkylation of an acylanion-equivalent.

  通过去质子化醛胺与2-(N-甲基苯胺)-丙烯腈的迈克尔加成制备1,4-酮醛 新的方法描述了通过一步法三组分偶联反应合成该标题化合物。该方法包括酮酸根离子和烯醇阳离子等价物的反应，随后对酰基阴离子等价物进行烷基化。
• Tandem-Michael-Addition von 1-Cyanenaminen an Cyclohexenone. Ein neuer Zugang zu Bicyclo[2.2.2]octanonen
  作者：Hubertus Ahlbrecht、Manfred Dietz、Claudia Schön、Volker Baumann

  DOI：10.1055/s-1991-26398

  日期：——

  Tandem-Michael Addition of 1-Cyanoenamines to Cyclohexenones A New Access to Bicyclo[2.2.2]octanones Bicyclo[2.2.2]octane-2,5-diones 5 are easily obtained via tandem Michael addition of 2-(N-methylanilino)acrylonitrile (2) with deprotonated cyclohexenones 1. The reaction is highly anti-stereoselective with respect to substituents on C-4 and C-5 of the cyclohexenone and is blocked by disubstitution on C-4. 6-Acylbicyclo[2.2.2]octan-2-ones 25 are obtained by tandem Michael addition of deprotonated 2-(N-methylanilino) but-2-enonitrile (18) with cyclohexenone and subsequent protonation or alkylation. Both reactions gave lower yields or even failed with cyclopentenone and cycloheptenone.

  1-氰基亚胺的串联迈克尔加成反应与环己烯酮的应用：获得双环[2.2.2]辛酮的新方法。双环[2.2.2]辛烷-2,5-二酮可通过2-(N-甲基苯胺基)丙烯腈与去质子化的环己烯酮的串联迈克尔加成反应轻松获得。该反应对于环己烯酮的C-4和C-5上的取代基具有高度的反超选择性，并且在C-4上存在双取代时会受到阻碍。6-酰基双环[2.2.2]辛烷-2-酮是通过去质子化的2-(N-甲基苯胺基)丁-2-烯腈与环己烯酮的串联迈克尔加成反应获得的，随后经历质子化或烷基化反应。这两种反应在环戊烯酮和环庚烯酮中都得到了较低的产率，甚至失败。
• Dienophilie des cyano-1 enamines, nouveaux equivalents de cetenes pour les cycloadditions de diels-alder
  作者：Jean-Luc Boucher、Lucien Stella

  DOI：10.1016/s0040-4020(01)96404-x

  日期：1985.1

  The Diels-Alder reactivity of two captodative olefins, 2-morpho-lino-acrylonitrile 15 and 2-(N-methlanilino) -acrylonitrile 16, towards four conjugated dienes is evaluated.In every cases, isomeric 4+2} cyclo-adducts are obtained.With olefin 15 yields are better than with olefin 16. The adducts are easily transformed in to the corresponding ketones by a mild hydrolysis of the α-aminonitrile group.

  评估了两种俘获性烯烃2-吗啉-亚麻基丙烯腈15和2-（N-甲基兰尼诺）-丙烯腈16对四个共轭二烯的Diels-Alder反应性。在每种情况下，异构体4 + 2}环加合物用烯烃15，其收率要好于用烯烃16。该加合物易于通过α-氨基腈基团的温和水解而转变成相应的酮。因此，可以将1-氰基烯胺视为对于不饱和环己酮的合成非常有用的良好的乙烯酮当量。

表征谱图