(2E,7E)-2,7-bis(3,4-dimethoxybenzylidene)cycloheptanone | 1148049-42-6

• 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: (2E,7E)-2,7-bis(3,4-dimethoxybenzylidene)cycloheptanone
• 英文别名: (E,E)-2,7-bis(3,4-dimethoxybenzylidene)cycloheptanone；2,7-Bis(3,4-dimethoxybenzylidene)cycloheptanone；(2E,7E)-2,7-bis[(3,4-dimethoxyphenyl)methylidene]cycloheptan-1-one
• CAS: 1148049-42-6
• 化学式: C₂₅H₂₈O₅
• 分子量: 408.494
• InChiKey: OVCPLBUUFUNPLX-IWGRKNQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 、 (2E,7E)-2,7-bis(3,4-dimethoxybenzylidene)cycloheptanone 在 溶剂黄146 作用下， 反应 24.0h， 以78%的产率得到ethyl (14E)-8-(3,4-dimethoxyphenyl)-14-[(3,4-dimethoxyphenyl)methylidene]-6-methyl-4-thia-2,7-diazatricyclo[7.5.0.03,7]tetradeca-1(9),2,5-triene-5-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of certain new thiazolo[2,3-b]quinazoline and thiazolo[3,2-a]pyrimidine analogs

  摘要：

  A novel series of thiazolo[2,3-b]quinazoline (16-19, 25-28, and 34-37) and cyclohepta[d]thiazolo[3,2-a]pyrimidine (20-23, 29-32, and 38-41) analogs was designed and synthesized. Structure elucidation of the synthesized compounds was attained by the use of H-1 NMR, C-13 NMR, and mass spectrometry. The obtained compounds were evaluated for their in vitro antitumor activity using the National Cancer Institute's 60 cell lines' panel assay that included nine tumor subpanels, namely, leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast cancer cells. Most of the investigated compounds showed a remarkable broad-spectrum antitumor activity. Compounds 19, 28, 32, and 34 proved to be 10-, 15-, 2-, and 7-fold more active than 5-FU, with GI(50) MG-MID values of 2.4, 1.5, 11.2, and 3.1 mu M, respectively.

  DOI：

  10.1007/s00044-013-0649-6
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (2E,7E)-2,7-bis(3,4-dimethoxybenzylidene)cycloheptanone
  参考文献：
  名称：

  Synthesis and antitumor activity of certain new thiazolo[2,3-b]quinazoline and thiazolo[3,2-a]pyrimidine analogs

  摘要：

  A novel series of thiazolo[2,3-b]quinazoline (16-19, 25-28, and 34-37) and cyclohepta[d]thiazolo[3,2-a]pyrimidine (20-23, 29-32, and 38-41) analogs was designed and synthesized. Structure elucidation of the synthesized compounds was attained by the use of H-1 NMR, C-13 NMR, and mass spectrometry. The obtained compounds were evaluated for their in vitro antitumor activity using the National Cancer Institute's 60 cell lines' panel assay that included nine tumor subpanels, namely, leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast cancer cells. Most of the investigated compounds showed a remarkable broad-spectrum antitumor activity. Compounds 19, 28, 32, and 34 proved to be 10-, 15-, 2-, and 7-fold more active than 5-FU, with GI(50) MG-MID values of 2.4, 1.5, 11.2, and 3.1 mu M, respectively.

  DOI：

  10.1007/s00044-013-0649-6

文献信息

• Study of in situ generation of carbocationic system from trityl chloride (Ph3CCl) which efficiently catalyzed cross-aldol condensation reaction
  作者：Abdolkarim Zare、Maria Merajoddin、Alireza Hasaninejad、Ahmad Reza Moosavi-Zare、Vahid Khakyzadeh

  DOI：10.1016/j.crci.2012.12.012

  日期：2013.4

  Résumé Organocatalyst trityl chloride (Ph3CCl), by in situ formation of trityl carbocation with inherent instability, efficiently promotes the cross-aldol condensation reaction between cycloalkanones and arylaldehydes in solvent-free and homogeneous media to afford α,α′-bis(arylidene)cycloalkanones in high yields. Moreover, an attractive and plausible mechanism based on observations and the literature is proposed for the reaction.

  简历 组织催化剂三苯氯甲烷（Ph3CCl）通过原位形成固有不稳定的三苯碳正离子，在无溶剂和均相介质中有效促进了环烷酮与芳香醛之间的交叉羟醛缩合反应，以高产率获得了α,α′-双(芳基亚甲基)环烷酮。此外，基于观察结果和文献，为该反应提出了一种吸引人的合理机理。
• Solvent-Free, Cross-Aldol Condensation Reaction Using Silica-Supported, Phosphorus-Containing Reagents Leading to α,α′-Bis(arylidene)cycloalkanones
  作者：Alireza Hasaninejad、Abdolkarim Zare、Laleh Balooty、Hadis Mehregan、Mohsen Shekouhy

  DOI：10.1080/00397910903457282

  日期：2010.11.3

  This article describes an efficient, simple, and clean method for the synthesis of alpha,alpha'-bis(arylidene, furylidene and cinnamylidene)cycloalkanones under solvent-free conditions. The cross-aldol condensation of cycloalkanones with aldehydes in the presence of silica-supported phosphorus pentoxide (P2O5/SiO2) or silicaphosphinoxide (silphox, [POCl3-n-(SiO2)(n)]) as heterogeneous reagents produces the title compounds in good to excellent yields.
• Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N. A. Nasr、Magda A. El-Sherbeny、Farid A. Badria、Laila A. Abou-zeid、Mariam A. Ghaly、Naglaa I. Abdel-Aziz

  DOI：10.1007/s00044-012-0116-9

  日期：2013.3

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.
• A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations
  作者：Nimisha Singh、Jyoti Pandey、Amit Yadav、Vinita Chaturvedi、Shalini Bhatnagar、Anil N. Gaikwad、Sudhir Kumar Sinha、Awaneet Kumar、P.K. Shukla、Rama P. Tripathi

  DOI：10.1016/j.ejmech.2008.09.026

  日期：2009.4

  An economical and facile synthesis of alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 mu g/mL. However, none of the compounds displayed any significant antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.
• HAMMAM, A. G., EGYPT. J. CHEM., 1982, 25, N 5, 471-480
  作者：HAMMAM, A. G.

  DOI：——

  日期：——