2-dimethylamino acrylonitrile | 34714-77-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-dimethylamino acrylonitrile
• 英文别名: dimethylaminomethyleneacetonitrile；Dimethylaminoacrylonitrile；2-(dimethylamino)prop-2-enenitrile
• CAS: 34714-77-7
• 化学式: C₅H₈N₂
• 分子量: 96.1319
• InChiKey: CRNHLPZBBWBNDN-UHFFFAOYSA-N

物化性质

• 沸点：
  63-64 °C(Press: 40 Torr)
• 密度：
  1.4550 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  7.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二叔丁基过氧化物 、 2-dimethylamino acrylonitrile 以 苯 为溶剂， 以59%的产率得到2,3-bis(dimethylamino)-2,3-bis[(2-methylpropan-2-yl)oxymethyl]butanedinitrile
  参考文献：
  名称：

  Preparative trapping of tert-butoxy radicals by captodative olefins

  摘要：

  DOI：

  10.1016/s0040-4039(01)90013-9
• 作为产物：
  描述：

  (N,N-Dimethylamino)methylmalondinitril 在 silica gel 作用下， 生成 2-dimethylamino acrylonitrile
  参考文献：
  名称：

  Plieninger,H. et al., Chemische Berichte, 1971, vol. 104, p. 3983 - 3985

  摘要：

  DOI：

文献信息

• α-Substituierte phosphonate—38
  作者：Burkhard Costisella、Hans Gross

  DOI：10.1016/0040-4020(82)85057-6

  日期：1982.1

  Alkylation of 1-dimethylamino-1-cyanomethanephosphonic acid diethyl ester (8), easily obtainable from diethyl phosphite and the 0,N-acetal 9, yields 1-alkyl derivatives 14. Elimination of HCN converts 14 into 1-phosphonoenamines 6. Carbonyl compounds react with 8 to give 1-cyanoenamines 15 which may be hydrolyzed to from the homologous carboxylic acid. Alternatively, deprotonation of 15 yields the homoenolate

  1-二甲基氨基-1-氰基甲烷膦酸二乙酯（8）的烷基化，可轻松地从亚磷酸二乙酯和0，N-乙缩醛9生成，生成1-烷基衍生物14。消除HCN可将14转化为1-膦烯胺6。羰基化合物与8反应生成1-氰基烯胺15，可以将其水解为同源羧酸。可选地，15的去质子化产生可以被烷基化或羟烷基化的均烯酸酯阴离子17，从而允许通过引入α-羧基和β-烷基而使羰基化合物的链增长。酸催化水解图8导致PC键的断裂，导致相应的α-二甲基氨基链烷酸。膦酸11可通过使用甲硅烷基酯法从8获得。氰基烯胺15的E / Z-异构体的明确分配是从13 C-NMR光谱中得出的。
• α-Cyclization of tertiary amines. Part 3. Captodative or push-pull enamines form pyrrolines, pyrrolizidines and their ring homologues with dimethyl acetylenedicarboxylate in a highly diastereoselective reaction
  作者：Benoît De Boeck、Shuiping Jiang、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/s0040-4020(01)85235-2

  日期：1994.1

  The title one-pot reaction occurs through a sequence of [2+2] cycloaddition, ring opening to dienamines and formation of a 1,5-dipole by [1,6] hydrogen-shift. This intermediate may cyclize or, in sterically suitable cases and at lower temperatures, lead to isolable N-vinyl enamines by proton transfer.

  通过[2 + 2]环加成，二烯胺开环和通过[1,6]氢转移形成1,5-偶极的过程发生标题一锅反应。该中间体可环化，或在空间上合适的情况下且在较低温度下通过质子转移产生可分离的N-乙烯基烯胺。
• 3-Phenyl-5-substituted-4(1H)-pyridones(thiones)
  申请人：Eli Lilly and Company

  公开号：US04152136A1

  公开（公告）日：1979-05-01

  A class of 3-phenyl-4(1H)-pyridones and pyridinethiones are broad-spectrum herbicides. The new compounds are characterized by a small substituent on the nitrogen, and usually bear a 5-substituent chosen from a class described herein. The phenyl ring may be substituted. The compounds are effective herbicides when applied both before and after the emergence of weeds, and are particularly useful for the control of weeds in cotton and rice cropland.

  一类3-苯基-4(1H)-吡啶酮和吡啉硫酮是广谱除草剂。这些新化合物的特点是氮上有一个小的取代基，并且通常带有从本文描述的一类中选择的5-取代基。苯环可能被取代。这些化合物在杂草出现之前和之后施用时是有效的除草剂，尤其适用于棉花和稻田的杂草控制。
• α-Cyclisation of tertiary amines. Part 4. Cyano-imidoyl substituted furans from captodative enamines and dibenzoylacetylene
  作者：Benoît De Boeck、Zdenek Janousek、Heinz G. Viehe

  DOI：10.1016/0040-4020(95)00821-o

  日期：1995.11

  α-Cyano-enamines and dibenzoylacetylene lead to dienes (via [2+2] cycloaddition followed by ringopening). Their α-Cyclisation to oxygen produces the title compounds.

  α-氰基-烯胺和二苯甲酰基乙炔导致二烯（通过[2 + 2]环加成，然后开环）。它们的α-环化成氧可生成标题化合物。
• N-aryl-4,5-diaminopyrazoles and dyes containing said compounds
  申请人：Goettel Otto

  公开号：US20050081312A1

  公开（公告）日：2005-04-21

  N-Aryl-4,5-diaminopyrazole of formula (I) or a physiologically compatible salt thereof of an organic or inorganic acid wherein R1 and R2 independently of each other denote a hydrogen atom, a straight-chain or branched C 1 -C 6 -alkyl group, a hydroxyl group, a straight-chain or branched C 1 -C 6 -monohydroxyalkyl group, a straight-chain or branched C 3 -C 6 -dihydroxyalkyl group, a straight-chain or branched C 1 -C 6 -alkoxy group, a straight-chain or branched C 1 -C 6 -hydroxyalkoxy group, a straight-chain or branched C 3 -C 6 -dihydroxyalkoxy group, an amino group, a C 1 -C 4 -monoalkylamino group, a di(C 1 -C 4 )-alkylamino group, a halogen atom, a difluoromethyl group or a trifluoromethyl group; Y stands for a nitrogen atom or a C—R3 group, wherein C is a carbon atom of the aromatic ring and R3 is a hydrogen atom, a halogen atom, a straight-chain or branched C 1 -C 6 -alkyl group, a straight-chain or branched C 1 -C 6 -hydroxyalkyl group, a straight-chain or branched C 1 -C 6 -alkoxy group, a straight-chain or branched C 2 -C 6 -hydroxyalkoxy group or a straight-chain or branched C 2 -C 6 -alkoxyalkoxy group; X denotes an acid radical and n has a value from 0 to 3; provided that when Y stands for a C—R3 group, at least one of the R1, R2 and R3 groups is different from hydrogen; as well as colorants for keratin fibers containing these compounds.

  式（I）的N-芳基-4,5-二氨基吡唑或其有机或无机酸的生理相容性盐，其中R1和R2独立地表示氢原子，直链或支链C1-C6烷基，羟基，直链或支链C1-C6单羟基烷基，直链或支链C3-C6双羟基烷基，直链或支链C1-C6烷氧基，直链或支链C1-C6羟基烷氧基，直链或支链C3-C6双羟基烷氧基，氨基，C1-C4单烷基氨基基，二(C1-C4)-烷基氨基基，卤原子，二氟甲基基或三氟甲基基; Y表示氮原子或C-R3基团，其中C是芳环的碳原子，R3是氢原子，卤原子，直链或支链C1-C6烷基，直链或支链C1-C6羟基烷基，直链或支链C1-C6烷氧基，直链或支链C2-C6羟基烷氧基或直链或支链C2-C6烷氧基烷氧基; X表示酸基团，n的值为0到3; 前提是当Y表示C-R3基团时，R1，R2和R3中至少有一个不同于氢;以及含有这些化合物的角蛋白纤维染料。