7-methoxy-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine | 1221422-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-methoxy-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine
• 英文别名: 7-Methoxy-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole；7-methoxy-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole
• CAS: 1221422-95-2
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: JLFYEQCSJNLNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine 在 硫酸 、 硝酸 作用下， 反应 24.0h， 以83%的产率得到7-methoxy-6,8-dinitro-1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole
  参考文献：
  名称：

  The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells

  摘要：

  Aziridinyl substituted benzimidazolequinones are more toxic than methoxy analogues towards normal human fibroblast cells (GM00637). The aziridinyl substituent is required for hypersensitive killing of Fanconi anaemia (FA) cells (PD20i) deficient in FANCD2. Despite lacking quinone functionality, 4,7-dimethoxy-N-[(aziridin-2-yl)methyl]benzimidazole also induces hypersensitivity from FA cells, similar to their response towards mitomycin C. Expression of FANCD2 (in PD20:RV) corrects FA cell hypersensitivity supporting cellular response via the FANC pathway. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.026
• 作为产物：
  描述：

  1-(4-甲氧基-2-硝基-苯基)-哌啶 在 甲酸 、 碘 作用下， 反应 8.0h， 以89%的产率得到7-methoxy-1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Formic acid as a sustainable and complementary reductant: an approach to fused benzimidazoles by molecular iodine-catalyzed reductive redox cyclization of o-nitro-t-anilines

  摘要：

  分子碘被发现是一种优秀的催化剂，可用于将o-硝基-t-苯胺还原氧化环化成融合的三环或1,2-二取代苯并咪唑。

  DOI：

  10.1039/c6gc00902f

文献信息

• Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones
  作者：Martin Sweeney、Michael Gurry、Lee-Ann J. Keane、Fawaz Aldabbagh

  DOI：10.1016/j.tetlet.2017.07.102

  日期：2017.9

  Environmentally-friendly and cost effective hydrogen peroxide in ethyl acetate was used to prepare in high yields pyrrolo[1,2-a]benzimidazoles from commercial o-(pyrrolidin-1-yl)anilines without the requirement for organic-aqueous extraction and chromatography. Six, seven and eight membered ring-fused analogues were similarly obtained in high yields with methanesulfonic acid required for the pyrido[1

  使用环境友好且经济高效的乙酸乙酯中的过氧化氢，无需有机水萃取和色谱法即可从商业邻-（吡咯烷基-1-基）苯胺制备高收率的吡咯并[1,2- a ]苯并咪唑。用吡啶[1,2- a ]苯并咪唑所需的甲磺酸，以高收率相似地获得了六，七和八元环稠合的类似物。通过3,6-二甲氧基-2-（环氨基）苯胺的环化，可以高产率获得抗肿瘤苯并咪唑醌衍生物。
• Metal-free construction of tricyclic or tetracyclic compounds—acid-promoted synthesis of benzo[4,5]imidazo[2,1-a]isoindole and 1,2-dialkyl-2,3-dihydrobenzimidazoles
  作者：Jinying Chen、Jinpeng Qu、Yuanqing Zhang、Yongxin Chen、Na Liu、Baohua Chen

  DOI：10.1016/j.tet.2012.10.030

  日期：2013.1

  An environmental friendly, efficient, and easy to operate strategy for synthesizing of benzo[4,5]imidazo [2,1-a]isoindole and 1,2-dialkyl-2,3-dihydrobenzimidazoles via acid-promoted coupling of dialdehyde and o-diaminobenzene under metal-free conditions is described. A series of products were generated in good yields under mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• Formic acid as a sustainable and complementary reductant: an approach to fused benzimidazoles by molecular iodine-catalyzed reductive redox cyclization of o-nitro-t-anilines
  作者：T. B. Nguyen、L. Ermolenko、A. Al-Mourabit

  DOI：10.1039/c6gc00902f

  日期：——

  Molecular iodine was found to be an excellent catalyst for reductive redox cyclization ofo-nitro-t-anilines1into fused tricyclic or 1,2-disubtituted benzimidazoles2.

  分子碘被发现是一种优秀的催化剂，可用于将o-硝基-t-苯胺还原氧化环化成融合的三环或1,2-二取代苯并咪唑。
• The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells
  作者：Karen Fahey、Liz O'Donovan、Miriam Carr、Michael P. Carty、Fawaz Aldabbagh

  DOI：10.1016/j.ejmech.2010.01.026

  日期：2010.5

  Aziridinyl substituted benzimidazolequinones are more toxic than methoxy analogues towards normal human fibroblast cells (GM00637). The aziridinyl substituent is required for hypersensitive killing of Fanconi anaemia (FA) cells (PD20i) deficient in FANCD2. Despite lacking quinone functionality, 4,7-dimethoxy-N-[(aziridin-2-yl)methyl]benzimidazole also induces hypersensitivity from FA cells, similar to their response towards mitomycin C. Expression of FANCD2 (in PD20:RV) corrects FA cell hypersensitivity supporting cellular response via the FANC pathway. (C) 2010 Elsevier Masson SAS. All rights reserved.