1-methyl-3-(ethoxycarbonylomethyl)benzimidazolium bromide | 52943-44-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-3-(ethoxycarbonylomethyl)benzimidazolium bromide
• 英文别名: 1-ethoxycarbonylmethyl-3-methyl-benzimidazolium bromide；ethyl 2-(3-methylbenzimidazol-3-ium-1-yl)acetate;bromide
• CAS: 52943-44-9
• 化学式: Br*C₁₂H₁₅N₂O₂
• 分子量: 299.167
• InChiKey: XIXJFKVPLNYXCB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.97
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(ethoxycarbonylomethyl)benzimidazolium bromide 生成 dimethyl 5-methyl-4-oxo-4,5-dihydropyrrolo[1,2-a]quinoxaline-2,3-dicarboxylate
  参考文献：
  名称：

  METH-COHN O., TETRAHEDRON LETT. , 1975, NO 6, 413-416

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基苯并咪唑 、 溴乙酸乙酯 以 乙酸乙酯 为溶剂， 反应 48.5h， 以78%的产率得到1-methyl-3-(ethoxycarbonylomethyl)benzimidazolium bromide
  参考文献：
  名称：

  氧化剂促进苯并咪唑鎓盐与烯烃的1,3-偶极环加成反应，制备4 H-吡咯并[1,2- a ]苯并咪唑

  摘要：

  开发了一种氧化剂促进苯并咪唑鎓烷基化物与烯烃的1,3-偶极环加成反应，用于在温和条件下以中等收率制备4 H-吡咯并[1,2- a ]苯并咪唑衍生物。在合适的氧化剂存在下，最商业上可买到的“正构”烯烃，而不是炔烃或“反常”烯烃，可以成功地用作双极性亲和剂。此外，在该程序中，已证明CrO 3 / Et 3 N是比MnO 2或重铬酸四基吡啶钴（II）更为有效的脱氢剂。

  DOI：

  10.1002/jhet.5570370620

文献信息

• Pyrroloquinoxalines
  申请人：Roussel Uclaf

  公开号：US04151280A1

  公开（公告）日：1979-04-24

  Novel pyrroloquinoxalines of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms and --NO.sub.2, Z is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms and phenyl and R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, ##STR2## and non-toxic, pharmaceutically acceptable cations, n is an integer from 1 to 6 and R.sub.1 and R.sub.2 are individually alkyl of 1 to 5 carbon atoms and the non-toxic, pharmaceutically acceptable acid addition salts thereof having antiallergic activity and to a novel process for their preparation.

  该专利描述了一种新型吡咯喹喔啉类化合物，化学结构如下：其中X和Y分别选自氢、卤素、1至5个碳原子的烷基和烷氧基以及--NO.sub.2的组合，Z选自1至8个碳原子的烷基、3至8个碳原子的环烷基、2至6个碳原子的烯基和苯基，R选自氢、1至5个碳原子的烷基、以及非毒性、药学上可接受的阳离子，n是1至6的整数，R.sub.1和R.sub.2分别为1至5个碳原子的烷基，以及具有抗过敏活性的非毒性、药学上可接受的酸盐，以及其制备的新方法。
• Crystal structure and physical properties of 1-methyl-3-(carboxymethyl)benzimidazolium betaine·CuBr₂ in crystal and water solution
  作者：Łukasz Czekański、Stanisław K. Hoffmann、Piotr Barczyński、Anna Gąsowska、Romualda Bregier-Jarzębowska、Alina Zalewska、Janina Goslar、Małgorzata Ratajczak-Sitarz、Andrzej Katrusiak

  DOI：10.1039/c6nj03192g

  日期：——

  molecule. NMR spectra confirm the coordination of Cu(II) ions and allow identification of H(2) proton as easily detached in basic conditions. FT-IR spectra confirm the unidentate coordination of the betaine carboxylate group. UV-Vis spectra show three bands in d–d-transition region. Energies of these transitions were used in the interpretation of the EPR results. From powder and single crystal EPR measurements

  合成并结晶了一种新的羧酸铜（Ⅱ）配位化合物[1-甲基-3-羧甲基苯并咪唑甜菜碱] 2 CuBr 2。晶体具有三斜对称性P，晶胞尺寸a = 7.9693，b = 8.4129，c = 9.1302Å，α = 68.058，β = 85.402和γ = 71.258度。（Z = 1），并且分子沿a轴堆叠。Cu（II）络合物是平面的，并且与生色团CuO 2 Br 2四配位，其中两个氧原子属于充当不明配体的两个甜菜碱的羧酸酯基团。通过二维1 H和13 C NMR光谱对化合物进行表征，以确定配体分子的质子之间的相关性。NMR光谱确认了Cu（II）离子的配位并允许在基本条件下容易分离H（2）质子。FT-IR光谱证实甜菜碱羧酸酯基团的不确定配位。紫外-可见光谱显示在d-d跃迁区域中的三个谱带。这些转换的能量被用于解释EPR结果。从粉末和单晶EPR测量，将g因子确定为g x＝ 2.072，g y＝ 2.030，g
• 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
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  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.
• A Novel 1,6 Cyclization of Imidazolium N-Allylides (1) : Formation of Mesomeric Betaines, 8-Oxoimidazo[1,2-a]pyridiniumides
  作者：Yoshiro Matsuda、Hiromi Gotou、Keisuke Katou、Hiroshi Matsumoto、Makoto Yamashita、Kimitoshi Takahashi、Shizuki Ide

  DOI：10.3987/com-90-5363

  日期：——
• Sepulveda-Arques, Jose; Arbiol, Eva Romero; Rosende, M. Eugenia Gonzalez, Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 7/8, p. 410 - 412
  作者：Sepulveda-Arques, Jose、Arbiol, Eva Romero、Rosende, M. Eugenia Gonzalez、Lopez-Rodriguez, Matias、Afonso, Ricardo Perez

  DOI：——

  日期：——