(1,3-二甲基-2-咪唑烷基亚基)-乙腈 | 178483-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (1,3-二甲基-2-咪唑烷基亚基)-乙腈
• 英文名称: 2-(cyanomethylene)-1,3-dimethylimidazoline
• 英文别名: 2-(1,3-Dimethylimidazolidin-2-ylidene)acetonitrile
• CAS: 178483-44-8
• 化学式: C₇H₁₁N₃
• 分子量: 137.184
• InChiKey: CYTNRGDYTSEJQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1,3-二甲基-2-咪唑烷基亚基)-乙腈 、 丙炔酸乙酯 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到1,3-dimethyl-2-(1-cyano-3-ethoxycarbonylprop-2-enylidene)-2,3,4,5-tetrahydroimidazole
  参考文献：
  名称：

  氮杂烯还是迈克尔加成？检查非常规取代基对杂环烯酮缩醛与丙酸乙酯反应的影响

  摘要：

  具有至少一个仲氨基的杂环烯酮缩醛在各种条件下与丙酸乙酯进行氮杂-烯键反应，生成相应的加合物，在有或没有乙醇钠回流的情况下，它们很容易转化为δ-内酰胺稠合的杂环产物乙醇，而酯和氰基取代的叔烯二胺则充当强迈克尔供体，可在极性或质子溶剂中添加到丙酸乙酯中。讨论了不同寻常的取代基对反应性和机理的影响。

  DOI：

  10.1016/s0040-4020(02)00002-9
• 作为产物：
  描述：

  2-cyano-3,3-bis(methylsulfanyl)prop-2-enoic acid 、 N,N'-二甲基乙二胺 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以50%的产率得到(1,3-二甲基-2-咪唑烷基亚基)-乙腈
  参考文献：
  名称：

  Sodium 2-Cyanoethylene-1,1-dithiolate Tetrahydrate: a Stable Salt of Cyanodithioacetic Acid. A New Preparative Route to 2-Cyanoketene S,S-, S,N- and N,N-Acetals.

  摘要：

  2-Cyanoethylene-1,1-dithiolate, the dianion of cyanodithioacetic acid, is prepared from ethyl cyanoacetate by condensation with carbon disulfide followed by hydrolysis and decarboxylation with sodium hydroxide. The anion has been isolated and characterized as a stable, tetrahydrated sodium salt (2) and alkylated to give 3,3-bis(alkylthio)propenonitriles (3) in excellent yields. Alkylation of an intermediate, unstable trianion of 2-cyano-1,1-dithiomalonic acid (4) gives 3,3-bis(methylthio)-2-cyanopropenic acid (6a) which on treatment with mono- and di-alkylamines undergoes consecutive substitution and decarboxylation to 3-amino-3-(methylthio)propenonitriles (7). The application of 1,2-diamines or 2-aminoethanethiol leads to cyclized products, (imidazolidin-2-ylidene) acetonitriles(9) and (1,3-thiazolidin-2-ylidene)acetonitrile (10), respectively.

  DOI：

  10.3891/acta.chem.scand.50-0432

文献信息

• The aza–ene or the Michael addition? Examination of an unusual substituent effect on the reaction of heterocyclic ketene aminals with ethyl propiolate
  作者：Mei-Xin Zhao、Mei-Xiang Wang、Zhi-Tang Huang

  DOI：10.1016/s0040-4020(02)00002-9

  日期：2002.2

  group underwent the aza–ene reaction with ethyl propiolate under various conditions to yield the corresponding adducts, which were readily transformed into the δ-lactam fused heterocyclic products with or without the aid of sodium ethoxide in refluxing ethanol, while the ester- and cyano-substituted tertiary enediamines acted as the strong Michael donor to add to ethyl propiolate in a polar or a protic

  具有至少一个仲氨基的杂环烯酮缩醛在各种条件下与丙酸乙酯进行氮杂-烯键反应，生成相应的加合物，在有或没有乙醇钠回流的情况下，它们很容易转化为δ-内酰胺稠合的杂环产物乙醇，而酯和氰基取代的叔烯二胺则充当强迈克尔供体，可在极性或质子溶剂中添加到丙酸乙酯中。讨论了不同寻常的取代基对反应性和机理的影响。
• Sodium 2-Cyanoethylene-1,1-dithiolate Tetrahydrate: a Stable Salt of Cyanodithioacetic Acid. A New Preparative Route to 2-Cyanoketene S,S-, S,N- and N,N-Acetals.
  作者：Lars Henriksen、Sten C. Hj. Ljunggren、Gitte B. Vaaben、Ali A. El-Emam、Erik B. Pedersen、Claus Nielsen、Shu Hai Zhao、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0432

  日期：——

  2-Cyanoethylene-1,1-dithiolate, the dianion of cyanodithioacetic acid, is prepared from ethyl cyanoacetate by condensation with carbon disulfide followed by hydrolysis and decarboxylation with sodium hydroxide. The anion has been isolated and characterized as a stable, tetrahydrated sodium salt (2) and alkylated to give 3,3-bis(alkylthio)propenonitriles (3) in excellent yields. Alkylation of an intermediate, unstable trianion of 2-cyano-1,1-dithiomalonic acid (4) gives 3,3-bis(methylthio)-2-cyanopropenic acid (6a) which on treatment with mono- and di-alkylamines undergoes consecutive substitution and decarboxylation to 3-amino-3-(methylthio)propenonitriles (7). The application of 1,2-diamines or 2-aminoethanethiol leads to cyclized products, (imidazolidin-2-ylidene) acetonitriles(9) and (1,3-thiazolidin-2-ylidene)acetonitrile (10), respectively.

表征谱图