1,3-二乙酰基-4,6-二甲氧基苯 | 3098-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3-二乙酰基-4,6-二甲氧基苯
• 英文名称: 1,1'-(4,6-dimethoxy-1,3-phenylene)diethanone
• 英文别名: 1-(5-acetyl-2,4-dimethoxyphenyl)-1-ethanone；5-acetyl-2,4-dimethoxyacetophenone；1,5-diacetyl-2,4-dimethoxy-benzene；1,5-Diacetyl-2,4-dimethoxy-benzol；1,3-Diacetyl-4,6-dimethoxy-benzol；4,6-Dimethoxy-1,3-diacetyl-benzol；1-(5-Acetyl-2,4-dimethoxyphenyl)ethanone
• CAS: 3098-67-7
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD01926551
• 分子量: 222.241
• InChiKey: NSPIPHLQGRBQKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1,3-二乙酰基-4,6-二甲氧基苯 在 盐酸 、 锌 作用下， 以 苯 为溶剂， 生成 2,4-diethyl-1,5-dimethoxybenzene
  参考文献：
  名称：

  Madeja-Kotkowska,Z., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1974, vol. 22, p. 365 - 375

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯二酚 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 1,3-二乙酰基-4,6-二甲氧基苯
  参考文献：
  名称：

  Synthesis and antimicrobial activity of bischalcone derivatives

  摘要：

  Several bischalcones (2a-h and 5a-e) and flavones (3a-f) were synthesized and evaluated for their antimicrobial actions. Bischalcones were prepared by condensing 1,1'-(4,6-dimethyl-1,3-phenylene)diethanone (1) or 1-(5-acetyl-2,4-dimethoxyphenyl)-1-ethanone (4) with arylaldehydes. Bischalcones were cyclized in presence of iodine to give corresponding flavones (3a-f). An alternative route to synthesize the flavones consisted in preparing the diester derivatives (6a-f) of (1) with different aromatic acids, which could be converted to beta-diketones followed by cyclization to give the corresponding flavones. However, all the attempts in this direction were unsuccessful and it could not be possible to proceed beyond diester stage; six diester derivatives (6a-f) were synthesized. The structures of the synthesized compounds were assigned on the basis of H-1 NMR, mass spectral data and microanalyses results. The antimicrobial screening was performed at a concentration of 100 mu g/mL by cup plate method; the compounds inhibiting growth of one or more of the microorganisms were further tested for their minimum inhibitory concentration (MIC) by turbidity method. Preliminary antimicrobial results revealed that the compounds 2a-h and 3a-f were significant in their antibacterial and antifungal activities. MICs results showed that the compound 2f exhibited very good activity against E. coli, P. aeruginosa, and C. albicans with MIC-12.5 mu g/mL. Similar type of activity was shown the compound 3a against S. aureus and C. albicans with MIC-12.5 mu g/mL. Another compound, 3f, was active against P. aeruginosa and C. albicans with MIC-12.5 mu g/mL. Methylation of the two chelated hydroxyls (5a-e) significantly reduced the activity. However, oxidative cyclization of bischalcones resulted in compounds (3a-f) which were found to be considerably active. Diesters (6a-f) were insignificant in their antimicrobial activities.

  DOI：

  10.1007/s00044-012-0137-4

文献信息

• Microwave Assisted Synthesis and Biological Activity of Novel Bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole} Derivatives
  作者：N. H. Kumar Baba、D. Ashok、Boddu Ananda Rao、Madderla Sarasija、N. Y. S. Murthy

  DOI：10.1134/s1070363218030301

  日期：2018.3

  Gramnegative stains. Some of the compounds 5b, 5f, 5h demonstrated high activity against B. subtilis (+ve), compound 5c exhibited high activity against E. coli (–ve) and P. aeruginosa (–ve) stains. Among the titled compounds also evaluated for their in vitro antimycobacterial activity, the product 5b demonstrated pronounced antimycobacterial activity against M. bovis stain.

  摘要—由相应的1，合成了新的4,4'-（4,6-二甲氧基-1,3-亚苯基）双2- [2-（取代的亚苄基）肼基]噻唑}衍生物（5a - 5j），通过常规方法并在微波辐射下，将1′-（4，6-二甲氧基-1，3-亚苯基）双（2，2-二溴乙酮）和取代的硫代半咔唑酮。合成的化合物的结构通过FT-IR，1H和13C NMR和质谱表征。评价产品对革兰氏阳性和革兰氏阴性菌的体外抗菌活性。化合物5b，5f和5h中的某些化合物表现出对枯草芽孢杆菌（+ ve），化合物5c的高活性对大肠杆菌（–ve）和铜绿假单胞菌（–ve）染色表现出高活性。在还评估了其体外抗分枝杆菌活性的标题化合物中，产物5b显示出针对牛分枝杆菌染色的显着的抗分枝杆菌活性。
• A Facile Demethylation of Ortho Substituted Aryl Methyl Ethers Promoted by AlCl₃
  作者：Zhen-Ting Du、Jing Lu、Hong-Rui Yu、Yan Xu、An-Pai Li

  DOI：10.3184/030823410x12708998015900

  日期：2010.4

  An efficient and practical demethylation of ortho substituted aryl methyl ethers using AlCl3 has been developed. This method gives a high conversion, is simple to operate and is cost-effective. A mechanism involving the complexation of AlCl3 with the OMe and the adjacent electron withdrawing group is proposed. Many functional groups can be tolerated in the demethylation process, and 29 examples gave

  已经开发出使用 AlCl3 对邻位取代的芳基甲基醚进行有效和实用的去甲基化。该方法转化率高，操作简单，成本低廉。提出了一种涉及 AlCl3 与 OMe 和相邻吸电子基团络合的机制。去甲基化过程中可以容忍许多官能团，29个例子以90-98％的产率得到了去甲基化产物。
• Leukotriene B4 receptor antagonists: the LY255283 series of hydroxyacetophenones
  作者：David K. Herron、Theodore Goodson、Nancy G. Bollinger、Dorothy Swanson-Bean、Ian G. Wright、Gilbert S. Staten、Alan R. Thompson、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00088a018

  日期：1992.5

  A series of hydroxyacetophenones was prepared for evaluation as leukotriene B4 (LTB4) receptor antagonists, culminating in 1-[5-ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazol-5- yl)heptyl]oxy]phenyl]ethanone (compound 35, LY255283). Using an assay for inhibition of specific [3H]LTB4 binding to human PMN, we found that substitution of a nonpolar substituent in the 5-position was required for activity.

  制备了一系列羟基苯乙酮作为白三烯B4（LTB4）受体拮抗剂进行评估，最终以1- [5-乙基-2-羟基-4-[[6-甲基-6-（1H-四唑-5-基）庚基] [氧基]苯基]乙酮（化合物35，LY255283）。使用抑制特异性[3H] LTB4与人PMN结合的测定方法，我们发现活性需要5位非极性取代基的取代。最佳活性是通过3位氢，2位羟基，1位短链烷基酮以及将4位氧与不饱和末端相连的六碳或八碳链实现的功能。选择在结合试验中IC50为87 nM的化合物35进行进一步的临床前评估。
• Microwave-assisted synthesis of bis(<i>N</i>-substituted thiazol-2-amine) derivatives and their biological activities
  作者：N.H. Kumar Baba、D. Ashok、Boddu Ananda Rao、Madderla Sarasija、N.Y.S. Murthy、Vankadari Srinivasarao、Tigulla Parthasarathy

  DOI：10.1515/hc-2017-0129

  日期：2017.10.26

  6-dimethoxy-1,3-phenylene)-bis(N-substituted thiazol-2-amine) derivatives 5a–j were synthesized from 1,1′-(4,6-dimethoxy-1,3-phenylene)-bis(2-bromoethanone) 3 and substituted thioureas 4a–j under conventional and microwave irradiation conditions. All products were subjected to in vitro antibacterial and anti-TB evaluation. Some of the compounds exhibit good activities against Bacillus subtilis (+ve)

  摘要 从 1,1'-(4,6-二甲氧基-1,3-亚苯基)-双(N-取代的噻唑-2-胺)衍生物 5a-j 合成了新的 4,4'-(4,6-二甲氧基-1,3-亚苯基)-双(N-取代的噻唑-2-胺)衍生物 5a-j -1,3-亚苯基)-双(2-溴乙酮) 3 和取代的硫脲 4a-j 在常规和微波辐射条件下。所有产品均经过体外抗菌和抗结核评价。一些化合物对枯草芽孢杆菌 (+ve)、大肠杆菌 (-ve) 菌株和结核分枝杆菌 H37Rv 表现出良好的活性。
• 368. Derivatives of 1 : 2 : 3 : 4-tetrahydroxybenzene. Part III. The synthesis of dill apiole, and the extension of the Dakin reaction
  作者：Wilson Baker、E. H. T. Jukes、C. A. Subrahmanyam

  DOI：10.1039/jr9340001681

  日期：——