1-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole | 120671-12-7

• 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-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole
• 英文别名: (E)-2-(ethoxycarbonylmethylene)-1-benzylimidazoline；ethyl (1-benzylimidazolidin-2-ylidene)acetate；ethyl (2E)-2-(1-benzylimidazolidin-2-ylidene)acetate
• CAS: 120671-12-7
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: ZFNCNMPHVXDNGD-JLHYYAGUSA-N

物化性质

• 沸点：
  406.6±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 168.0h， 以100%的产率得到1-苄基-2-甲基-2-咪唑啉
  参考文献：
  名称：

  Alkylation of an imidazolidine enaminoester: A new sequence for the Cα-alkylation of 4,5-dihydroimidazoles

  摘要：

  1-Benzyl-2-(ethoxycarbonylmethylene)-2,3 undergoes preferred C-alkylation with halogenoalkanes, dihalogenoalkanes and epoxides: subsequent removal of of the ethoxycarbonyl group provides a new route to 2-alkyl-4,5-dihydroimidazoles. 1,3-Dihalogenoalkanes afford imidazo[1,2-a]pyridines via C,N-dialkylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00752-7
• 作为产物：
  描述：

  N-苄基乙二胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole
  参考文献：
  名称：

  Anderson, Michael W.; Begley, Michael J.; Jones, Raymond C. F., Journal of the Chemical Society. Perkin transactions I, 1984, # 11, p. 2599 - 2602

  摘要：

  DOI：

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。
• Perkin communications. A new sequence for the C^α-alkylation of 4,5-dihydroimidazoles
  作者：Raymond C. F. Jones、Simon C. Hirst、Ian Turner

  DOI：10.1039/p19910000953

  日期：——

  The C-alkylation of 1-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole with halogeno- and dihalogeno-alkanes is described; subsequent removal of the ethoxycarbonyl group provides a new route to 2-alkyl-4,5-dihydroimidazoles. 1,3-Dihalogenoalkanes afford imidazo[1,2-a]pyridines.
• Annulation of imidazolines with bis-electrophiles: Synthesis of imidazo[1,2-a]pyridines
  作者：Raymond C.F. Jones、Pravin Patel、Simon C Hirst、Mark J Smallridge

  DOI：10.1016/s0040-4020(98)00312-3

  日期：1998.5

  1-Benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole undergoes annulation with a variety of 1,3-bis-electrophiles (alpha,beta-unsaturated acid derivatives, beta-ketoesters, se-unsaturated aldehydes) to form imidazo[1,2-a]pyridines. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-α expression in T cells
  作者：Jan Rether、Gerhard Erkel、Timm Anke、Johan Bajtner、Olov Sterner

  DOI：10.1016/j.bmc.2007.10.074

  日期：2008.2.1

  Novel hexahydroimidazo[1,2-a]pyridines prepared by the addition of ethyl (1-benzylimidazolidin-2-ylidene)acetate (2) to the fungal metabolite podoscyphic acid (1a) and esters of la have been evaluated for their ability to inhibit the inducible TNF-alpha promoter activity in T cells. The methyl ester 3b is the most potent, inhibiting the TNF-alpha driven reporter gene expression in Jurkat T cells with an IC50-value of 2.0 mu g/ml (3.6 mu M). In addition, compound 3b inhibited the inducible TNF-alpha production in the myelomonocytic U937 cells with an IC50-value of 4.6 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
• JONES, RAYMOND C. F.;HIRST, SIMON C., TETRAHEDRON LETT., 30,(1989) N9, C. 5361-5364
  作者：JONES, RAYMOND C. F.、HIRST, SIMON C.

  DOI：——

  日期：——