2-(3,4-Dimethoxybenzyliden)cyclohexanon | 88692-77-7

• 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: 2-(3,4-Dimethoxybenzyliden)cyclohexanon
• 英文别名: (E)-2-(3,4-dimethoxybenzylidene)cyclohexanone；(2E)-2-[(3,4-dimethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 88692-77-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: XHEXTNNXHJUONB-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-Dimethoxybenzyliden)cyclohexanon 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 potassium acetate 、 sodium acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 4-(3,4-dimethoxyphenyl)-2,3-diphenyl-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  氧化还原-中性钴（III）催化的α，β-不饱和肟醚与炔烃的C–H活化/环化：一步到达多取代吡啶

  摘要：

  据报道，α，β-不饱和肟醚与炔烃的氧化还原中性Co（III）催化环化。多取代的吡啶以高收率合成，无需使用任何重金属氧化剂。所开发的方法可以容忍各种功能组。值得注意的是，该转化已应用于生物活性分子脱氢孕烯醇酮的后期修饰。

  DOI：

  10.1021/acs.joc.0c02558
• 作为产物：
  描述：

  1-吗啉基-1-环己烯 、 3,4-二甲氧基苯甲醛 以60%的产率得到2-(3,4-Dimethoxybenzyliden)cyclohexanon
  参考文献：
  名称：

  Osske, G.; Szabo, D.; Lorand, T., Pharmazie, 1988, vol. 43, # 3, p. 164 - 165

  摘要：

  DOI：

文献信息

• Synthesis and antibacterial study of unsaturated Mannich ketones
  作者：Tamás Lóránd、Béla Kocsis、Pál Sohár、Gergely Nagy、Gyula Kispál、Hans-Georg Krane、Horst Schmitt、Edgar Weckert

  DOI：10.1016/s0223-5234(01)01264-8

  日期：2001.9

  Several Mannich ketones of 2-arylmethylenecycloalkanones were synthesised using the classical acid-catalysed Mannich reaction. Antibacterial activity of these new water-soluble compounds was reported against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Staphylococcus saprophyticus, Micrococcus luteus and Bacillus subtilis standard strains. Human cell line cytotoxicity of our new compounds was evaluated against HeLa cell lines. Some compounds showed low cytotoxicity (41.52 nM mL(-1) for 14 and 46.60 nM mL(-1) for 18) and proved to be efficient antibacterial agents against the Gram-positive strains. Minimum inhibitory concentrations varied from 1.56 to 100 mug mL(-1). The mechanism of action was examined, too. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• Osske, G.; Szabo, D.; Lorand, T., Pharmazie, 1988, vol. 43, # 3, p. 164 - 165
  作者：Osske, G.、Szabo, D.、Lorand, T.

  DOI：——

  日期：——
• OSSKE, G.;SZABO, D.;LORAND, T., PHARMAZIE, 43,(1988) N 3, 164-165
  作者：OSSKE, G.、SZABO, D.、LORAND, T.

  DOI：——

  日期：——
• Discovery of new MD2-targeted anti-inflammatory compounds for the treatment of sepsis and acute lung injury
  作者：Gaozhi Chen、Bing Xiao、Lingfeng Chen、Bin Bai、Yali Zhang、Zheng Xu、Lili Fu、Zhiguo Liu、Xiaokun Li、Yunjie Zhao、Guang Liang

  DOI：10.1016/j.ejmech.2017.08.036

  日期：2017.10

  Myeloid differentiation 2 (MD2) is essential to the recognition of lipopolysaccharide (LPS) and the subsequent mediation of toll-like receptor 4 (TLR4)-dependent acute inflammatory disorders including sepsis and acute lung injury. Inhibitors targeting MD2 may provide an alternative means to subdue acute inflammatory diseases. In the present study, 39 bisaryl-1,4-dien-3-one compounds with 5-carbon connection chains were designed and synthesized as MD2 inhibitors based on the analysis of the molecular docking of xanthohumol to MD2. The compound-MD2 interactions were measured by cell-free assays including bis-ANS displacement and SPR, and the active compounds were further tested for MD2 inhibition and anti-inflammatory activities in LPS-challenged macrophages. The most active compound, 1f, was shown to have remarkable protective effects against sepsis shock and pulmonary inflammation. Collectively, we present evidence that bisaryl-1,4-dien-3-one is a new lead structure for the development of anti-inflammatory agents targeting MD2. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Redox-Neutral Cobalt(III)-Catalyzed C–H Activation/Annulation of α,β-Unsaturated Oxime Ether with Alkyne: One-Step Access to Multisubstituted Pyridine
  作者：Smruti Ranjan Mohanty、Bedadyuti Vedvyas Pati、Shyam Kumar Banjare、Gopal Krushna Das Adhikari、Ponneri Chandrababu Ravikumar

  DOI：10.1021/acs.joc.0c02558

  日期：2021.1.1

  A redox neutral Co(III)-catalyzed annulation of α,β-unsaturated oxime ether with alkyne has been reported. Multisubstituted pyridines were synthesized in good yields without the use of any heavy metal oxidants. The developed methodology tolerates a variety of functional groups. Notably, this transformation has been applied to the late-stage modification of the bioactive molecule dehydropregnenolone

  据报道，α，β-不饱和肟醚与炔烃的氧化还原中性Co（III）催化环化。多取代的吡啶以高收率合成，无需使用任何重金属氧化剂。所开发的方法可以容忍各种功能组。值得注意的是，该转化已应用于生物活性分子脱氢孕烯醇酮的后期修饰。