咪唑并[2,1-a]异喹啉-2-羧酸乙酯 | 69707-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 咪唑并[2,1-a]异喹啉-2-羧酸乙酯
• 英文名称: Imidazo[2,1-a]isoquinoline-2-carboxylic acid ethyl ester
• 英文别名: Ethyl imidazo[2,1-a]isoquinoline-2-carboxylate
• CAS: 69707-18-2
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: SJPJZLTUCNZIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  咪唑并[2,1-a]异喹啉-2-羧酸乙酯 在 一水合肼 作用下， 反应 0.33h， 以96%的产率得到Imidazo[2,1-a]isoquinoline-2-carboxylic acid hydrazide
  参考文献：
  名称：

  咪唑并[2,1-α]异喹啉衍生物的研究。2.咪唑并[2,1-α]异喹啉系列酯的合成与转化

  摘要：

  DOI：

  10.1007/bf00501830
• 作为产物：
  描述：

  1-氨基异喹啉 在 乙醇 作用下， 生成 咪唑并[2,1-a]异喹啉-2-羧酸乙酯
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009

文献信息

• Novel α,α-Difluorohomophthalimides via Copper-Catalyzed Tandom Cross-Coupling−Cyclization of 2-Halobenzamides with α,α-Difluoro Reformatskii Reagent
  作者：Yijun Pan、Christopher P. Holmes、David Tumelty

  DOI：10.1021/jo050599r

  日期：2005.6.1

  Novel α,α-difluorohomophthalimides 2 were prepared by reacting N-substituted 2-halobenzamides with the α,α-difluoro Reformatskii reagent BrZnCF2CO2Et (3) in the presence of CuBr at room temperature. The synthesis involves a CuBr-mediated cross-coupling of 3 with aryl iodides or activated aryl bromides, followed by a spontaneous cyclization of the ethyl 2-benzamido-α,α-difluoroacetate intermediates

  新颖α，α-difluorohomophthalimides 2通过反应制备ñ -取代2-卤代苯甲酰胺与α，α-二氟Reformatskii试剂BrZnCF 2 CO 2的Et（3）中的CuBr的在室温下的存在。合成过程涉及CuBr介导的3与芳基碘化物或活化的芳基溴化物的交叉偶联，然后在室温下自生环化2-苯甲酰胺基-α，α-二氟乙酸乙酯中间体。还通过使3当量的3进行反应，制备了带有能够充当羧酸生物等排体的酸性酰亚胺质子的N-未取代的α，α-二氟邻苯二甲酰亚胺2（R'= H）。与母体2-碘苯甲酰胺。其他芳基碘化物，例如3-碘-咪唑并[1,2-α]吡啶也用于串联偶联-环化反应。
• KUZMENKO T. A.; KUZMENKO V. V.; SIMONOV A. M.; SIMKIN B. YA., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 12, 1656-1661
  作者：KUZMENKO T. A.、 KUZMENKO V. V.、 SIMONOV A. M.、 SIMKIN B. YA.

  DOI：——

  日期：——
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——