(E)-2-(3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: 2-[(E)-3-nitrophenylmethylidene]-1-indanone；E-2-(3'-nitrobenzylidene)-1-indanone；2-(3-(Hydroxy(oxido)amino)benzylidene)-1-indanone；(2E)-2-[(3-nitrophenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: YBBSELSAFWNGFE-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one 生成 3-(2,3-dihydro-1H-inden-2-ylmethyl)aniline
  参考文献：
  名称：

  SCHIRMER, U.;PLATH, P.;WUERZER, B.

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯甲醛 、 1-茚酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-2-(3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  3-异硫氰酸酯基羟吲哚与环外α，β不饱和酮的对映选择性催化级联迈克尔/环化反应途中到-3,2'-吡咯烷基bispirooxindoles †

  摘要：

  研究表明，在存在奎宁衍生的叔氨基-方酸酰胺催化剂的情况下，3-异硫氰酸根合吲哚与环外α，β-不饱和酮之间的级联迈克尔/环化反应可以有效地进行，并提供包含两个螺-季四元的3,2'-吡咯烷基二螺氧基辛多烯和三个连续的立体中心，作为单一的非对映异构体，具有出色的对映选择性（最高99：1 er）。

  DOI：

  10.1039/c6ob02187e

文献信息

• Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles
  作者：Satavisha Kayal、Santanu Mukherjee

  DOI：10.1039/c6ob02187e

  日期：——

  Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters as a single diastereomer with excellent enantioselectivities (up to 99 : 1

  研究表明，在存在奎宁衍生的叔氨基-方酸酰胺催化剂的情况下，3-异硫氰酸根合吲哚与环外α，β-不饱和酮之间的级联迈克尔/环化反应可以有效地进行，并提供包含两个螺-季四元的3,2'-吡咯烷基二螺氧基辛多烯和三个连续的立体中心，作为单一的非对映异构体，具有出色的对映选择性（最高99：1 er）。
• Synthesis of Highly Functionalised Dispiropyrrolidine Derivatives as Novel Acetylcholinesterase Inhibitors
  作者：Ang Chee Wei、Mohamed Ashraf Ali、Yeong Keng Yoon、Rusli Ismail、Tan Soo Choon、Kooi-Yeong Khaw、Vikneswaran Murugaiyah、Venu Sanjeevi Lakshmipathi

  DOI：10.2174/15701808113109990038

  日期：2013.12.31

  In the effort of finding novel acetyl cholinesterase (AChE) inhibitors to improve the efficacy of Alzheimer’s disease (AD) treatment, series of substituted aryl-1´-methyldispiro[indan-2,2´ pyrrolidine-3´,2-indan]-1,3,1-trione and substituted 7´-aryl-5´,6´,7´,7a´-tetrahydrodispiro-[indane-2,5´-pyrrolo[1,2-c][1,3]thiazole-6´,2-indan]-1,3,1-trione analogues were synthesized using [3+2]-cycloaddition reactions. These newly synthesized pyrrolidine compounds were assayed for their biological activity using Ellman’s method. The structural elucidation of the compounds was performed by using 1H-NMR, 13C-NMR, ESI-MS spectra and elemental analyses. Eight out of twenty synthesized compounds showed more than 50% inhibition at concentration of 10 µM. Compound 2e, 2i and 3e were among the most active one, giving IC50 value as 3.3 M for 2e, 3.7 µM for 2i and 5.5 µM for 3e, respectively. Lineweaver-Burk plot indicated that 2i inhibits AChE in a competitive manner. Molecular modelling study was performed to disclose the binding interaction of these compounds with the active site of AChE.

  为了寻找新型乙酰胆碱酯酶（AChE）抑制剂以提高阿尔茨海默病（AD）的疗效，一系列取代的芳基-1´-甲基二螺[茚-2,2´-吡咯烷-3´、2-茚满]-1,3,1-三酮和取代的 7´-芳基-5´,6´,7´,7a´-四氢二螺[茚满-2,5´-吡咯并[1,2-c][1,3]噻唑-6´,2-茚满]-1,3,1-三酮类似物。这些新合成的吡咯烷化合物采用埃尔曼法进行了生物活性检测。利用 1H-NMR、13C-NMR、ESI-MS 图谱和元素分析对这些化合物进行了结构阐释。在浓度为 10 µM 的 20 个合成化合物中，有 8 个化合物的抑制率超过 50%。其中，化合物 2e、2i 和 3e 的活性最高，其 IC50 值分别为 3.3 M（2e）、3.7 µM（2i）和 5.5 µM（3e）。Lineweaver-Burk 图表明，2i 以竞争方式抑制 AChE。分子建模研究揭示了这些化合物与 AChE 活性位点的结合相互作用。
• An Efficient and Regiospecific Synthesis of New 2,2′-Bipyridine Derivatives in Water
  作者：Shujiang Tu、Bo Jiang、Changsheng Yao、Hong Jiang、Junyong Zhang、Runhong Jia、Yan Zhang

  DOI：10.1055/s-2007-966014

  日期：2007.5

  An environmentally benign approach for the efficient microwave-assisted synthesis of new 2,2′-pyridine derivatives in water by the multicomponent reaction of an aldehyde, indane-1,3-dione, 2-acetylpyridine, and ammonium acetate is reported. It is an efficient and promising synthetic strategy for the construction of the 2,2′-bipyridine skeleton.

  报道了一种环境友好的方法，通过醛、茚满-1,3-二酮、2-乙酰基吡啶和乙酸铵的多组分反应，在水中有效地微波辅助合成新的 2,2'-吡啶衍生物。这是构建2,2'-联吡啶骨架的一种有效且有前景的合成策略。
• Antimycobacterial activity: A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines
  作者：Ang Chee Wei、Mohamed Ashraf Ali、Yeong Keng Yoon、Rusli Ismail、Tan Soo Choon、Raju Suresh Kumar、Natarajan Arumugam、Abdulrahman I. Almansour、Hasnah Osman

  DOI：10.1016/j.bmcl.2012.06.047

  日期：2012.8

  A series of twelve dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H(37)Rv and INH resistant M. tuberculosis strains using agar dilution method, four of them showed good activity with MIC of less than 1 mu M. Compound 4'-[5-(4-fluorophenyl) pyridin-3-yl]-1'-methyldispiro[indan-2,2' pyrrolidine-3',2 ''-indan]-1,3,1 ''-trione (4b) was found to be the most active with MIC of 0.1215 and 5.121 mu M, respectively. (c) 2012 Elsevier Ltd. All rights reserved.
• A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents
  作者：Ang Chee Wei、Mohamed Ashraf Ali、Yeong Keng Yoon、Rusli Ismail、Tan Soo Choon、Raju Suresh Kumar

  DOI：10.1016/j.bmcl.2012.12.069

  日期：2013.3

  A series of fourteen dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions and were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv in HTS (High Throughput Screen). Most of the compounds showed moderate to good activity with MIC of less than 20 mu M. Compound 4'-(4-bromophenyl)-1'-methyldispiro[acenaphthylene-1,2'-pyrrolidine-3',2 ''-indane]-2',1 ''(1H)-dione (4c) was found to be the most active with MIC of 12.50 mu M. (c) 2013 Elsevier Ltd. All rights reserved.