1-methyl-2-(benzoylmethylene)imidazoline | 124927-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-2-(benzoylmethylene)imidazoline
• 英文别名: 2-Phenacylidene-1-methylimidazolidine；(2E)-2-(1-methylimidazolidin-2-ylidene)-1-phenylethanone
• CAS: 124927-47-5
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: OFNZNOUQHFYJGA-FMIVXFBMSA-N

物化性质

• 沸点：
  331.9±42.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(benzoylmethylene)imidazoline 、 溴丙酮 在 4 A molecular sieve 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以72%的产率得到(1,5-Dimethyl-2,3-dihydropyrrolo[1,2-a]imidazol-7-yl)-phenylmethanone
  参考文献：
  名称：

  杂环烯酮胺与 α-溴酮的反应：吡咯稠合 1,3-二氮杂杂环的便捷合成

  摘要：

  杂环乙烯酮缩醛胺与α-溴酮反应得到C-烷基化杂环乙烯酮缩醛胺中间体，该中间体经过快速缩合反应生成吡咯稠合的1,3-二氮杂杂环化合物。

  DOI：

  10.1055/s-2000-7098
• 作为产物：
  描述：

  3,3-双甲基磺酰基-1-苯丙酮 、 N-甲基乙二胺 以 甲苯 为溶剂， 反应 6.0h， 以72%的产率得到1-methyl-2-(benzoylmethylene)imidazoline
  参考文献：
  名称：

  A New Route to 3H-1,5-Benzodiazepines and Heterocylic Ketene Aminals from Benzoyl Substituted Ketene Dithioacetals and Diamines

  摘要：

  异环酮亚胺5或3H-1,5-苯二氮杂萘4是通过苯甲酰取代的酮二硫代乙酸酯1与各种二胺2反应获得的。讨论了这两种不同产物的形成机制。

  DOI：

  10.1055/s-1992-26356

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。
• The Aza-ene Reaction of Heterocyclic Ketene Aminals with 4-Phenyl-1,2,4-triazoline-3,5-dione
  作者：Jian-Heng Zhang、Mei-Xiang Wang、Zhi-Tang Huang

  DOI：10.1039/a801566j

  日期：——

  Heterocyclic ketene aminals bearing a secondary enamine moiety underwent an efficient aza-ene reaction with 4-phenyl-1,2,4-triazoline-3,5-dione under very mild conditions, while no reaction was observed with their tertiary enamine analogues.

  具有仲烯胺部分的杂环烯酮缩醛在非常温和的条件下与4-苯基-1,2,4-三唑啉-3,5-二酮进行了有效的氮杂烯反应，而未发现与叔烯胺类似物发生反应。
• S_RN1 Arylation of Some Heterocyclic Ketene Aminals with 2,4-Dinitrohalobenzenes
  作者：Wen-Yi Zhao、Zhi-Tang Huang

  DOI：10.1080/00397919308012586

  日期：1993.9

  Abstract the anion of heterocyclic ketene aminals 1 - 4 reacted with 2, 4-dinitrohalobenzenes 5 to give the monoarylated products 6, 7, 9 and 11 by a SRN1 mechanism. In some cases, the diarylated products 8 and 10 were also isolated.

  摘要杂环烯酮缩醛胺 1 - 4 的阴离子与 2​​, 4-二硝基卤代苯 5 反应，通过 SRN1 机制得到单芳基化产物 6、7、9 和 11。在某些情况下，二芳基化产物 8 和 10 也被分离出来。
• Huang, Zhi-tang; Liu, Zhi-rong, Synthetic Communications, 1989, vol. 19, # 5and6, p. 943 - 958
  作者：Huang, Zhi-tang、Liu, Zhi-rong

  DOI：——

  日期：——
• The reaction of benzoyl-substituted heterocyclic ketene aminals with aryl azides
  作者：Zhitang Huang、Meixiang Wang

  DOI：10.1021/jo00027a035

  日期：1992.1

  The reaction between heterocyclic ketene animals, 2-(benzoylmethylene)imidazolidines 3, -hexahydropyrimidines 4, and phenyl azides 5 was investigated. Both the reaction rate and products were strongly dependent on the substituents on 3 or 4 and 5. The reaction rate decreased with the decrease of the electron-withdrawing ability of the Y on the aryl azide 5 with the order NO2 > Cl > H > CH3O, as well as with the decrease of the electron-donating ability of the X on the 3 or 4 following the order CH3O > CH3 > H > Cl. Substituents X and Y affected the course of the reaction. Thus, 3 or 4 reacted with p-nitrophenyl azide 5a to give exclusively highly substituted 1,2,3-triazole derivatives 6aa-da and 7aa-da. The reaction between 3 or 4 and other aryl azides 5b-d afforded respectively fused triazoles 8a-d or 9a-d (6-31%) in addition to triazoles 6ab-bd or 7ab-bd (8-76%). It is concluded that 3 and 4 behave mostly as nucleophiles rather than 1,3-dipolarophiles in reaction with aryl azides 5. Only in the case of unfavorable electronic factors may 3 and 4 act as 1,3-dipolarophiles toward 5.