2-(3,4-dimethoxyphenylmethylene)cyclohexanone | 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-dimethoxyphenylmethylene)cyclohexanone
• 英文别名: 2-Veratryliden-cyclohexanon；2-veratrylidene-cyclohexanone；2-(3',4'-dimethoxyphenylmethylene)cyclohexan-1-one；2-[(3,4-Dimethoxyphenyl)methylidene]cyclohexan-1-one
• CAS: 88692-77-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: XHEXTNNXHJUONB-UHFFFAOYSA-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：

  3,5-二甲氧基苯甲醛 、 2-(3,4-dimethoxyphenylmethylene)cyclohexanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以29.33%的产率得到2-(3,4-dimethoxybenzylidene)-6-(3,5-dimethoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro

  摘要：

  In the present study, a series of forty-five asymmetrical meta-methoxylated diarylpentanoids have been synthesized, characterized and evaluated for their in-vitro anti-cancer potential. Among the forty-five analogs, three compounds (20, 33 and 42) have been identified as lead compounds due to their excellent inhibition against five human cancer cell lines including SW620, A549, EJ28, HT1080 and MCF-7. Structure-activity relationship study on cytotoxicity of tested compounds suggested that the presence of meta-oxygenated phenyl ring played a critical role in enhancing their cytotoxic effects. Compounds 33 and 42 in particular, exhibited strongest cytotoxicity against tested cell lines with the IC50 values ranging from 1.1 to 4.3 M. Subsequent colony formation assay on SW620 cell line showed that both compounds 33 and 42 possessed strong anti-proliferative activity. In addition, flow cytometry based experiments revealed that these compounds could trigger intracellular ROS production thus inducing G2/M-phase cell arrest and apoptosis. All these results suggested that poly meta-oxygenated diarylpentnoid is a promising scaffold which deserved further modification and investigation in the development of natural product based anti-cancer drug. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.039
• 作为产物：
  描述：

  2-[(4,5-dimethoxyphenyl)(2-naphthylamino)methyl]cyclohexanone 在 盐酸 作用下， 生成 2-(3,4-dimethoxyphenylmethylene)cyclohexanone 、 2-萘胺
  参考文献：
  名称：

  摘要：

  Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, H-1 NMR, and mass spectra of the synthesized compounds were discussed.

  DOI：

  10.1023/a:1012355506689

文献信息

• Modified calcium oxide as stable solid base catalyst for Aldol condensation reaction
  作者：YING TANG、JINGFANG XU、XUEFAN GU

  DOI：10.1007/s12039-013-0362-5

  日期：2013.3

  A highly efficient and stable solid-base catalyst for Aldol condensation was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyse the Aldol condensation of cyclohexanone and benzaldehyde, as well as various benzaldehydes, to produce 2-benzylidenecyclohexanone with a good selectivity and high yield. Higher yield of 95.8% was obtained over modified CaO after 3 h, which is short compared with the yield of 92.1% after 12 h over commercial CaO. The influence of several reaction parameters, such as temperature, catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic centres of modified CaO are stable for CO2 and moisture. From the results of Fourier transform-infrared (FT-IR) and Thermogravity analysis (TG) characterization, the modifier was bonded on surface of CaO chemically and almost no Ca(OH)2 formed during the modification process. The type of aldehyde has great influence on the yield of aldol condensation.

  一种高效稳定的固体碱催化剂用于阿尔多尔缩合反应，通过简单地用溴化苄修饰商业氢氧化钙（CaO）制备而成。研究发现，改性后的CaO能够有效催化环己酮与苯甲醛及各种苯甲醛的阿尔多尔缩合，生成2-苄基环己酮，具有良好的选择性和高产率。在3小时内，改性CaO的产率达到95.8%，相比之下，商业CaO在12小时后的产率仅为92.1%。还研究了温度、催化剂负载等多种反应参数的影响。对改性CaO的湿度测试表明，其基本中心对二氧化碳和水分是稳定的。通过傅里叶变换红外光谱（FT-IR）和热重分析（TG）表征的结果显示，修饰剂与CaO表面发生了化学结合，并且在修饰过程中几乎没有形成Ca(OH)2。醛的种类对阿尔多尔缩合的产率有很大影响。
• Cycloalkane derivatives and fodder compositions containing the same
  申请人：Egyt Gyogyszervegyeszeti Gyar

  公开号：US04587261A1

  公开（公告）日：1986-05-06

  The invention relates to new cycloalkane derivatives, a process for the preparation thereof and compositions--particularly feed additives and animal feeds--containing the same. The new compounds of the present invention correspond to the general formula I ##STR1## wherein n is 3, 4, 5 or 6; R denotes a phenyl group optionally carrying one or more substituent/s/ selected from the group consisting of halogen, lower alkoxy and lower alkyl; R.sup.1 and R.sup.2 each represent hydrogen or form together a valence bond; R.sup.3 represents lower alkoxy or a phenyl optionally substituted by one or more C.sub.1-12 alkoxy. The fodder additives and fodders according to the invention contain as active ingredient an amount of 1 ppm to 85% by weight of a compound of the general formula I in admixture with inert solid or liquid carriers or diluents and can be used to advantage in animal husbandry.

  本发明涉及新的环烷衍生物、其制备方法以及包含它们的组合物，特别是饲料添加剂和动物饲料。本发明的新化合物对应于一般式I，其中n为3、4、5或6；R表示苯基，可选择携带来自卤素、低级烷氧基和低级烷基等基团中的一个或多个取代基；R1和R2分别表示氢或形成一个价键；R3表示低级烷氧基或一苯基，可选择通过一个或多个C1-12烷氧基进行取代。本发明的饲料添加剂和饲料包含一定量的一般式I化合物作为活性成分，其含量为1 ppm至85%重量与惰性固体或液体载体或稀释剂混合使用，并可在动物饲养中得到优化应用。
• Bicyclic Dihydropyrans by the Diels-Alder Reaction
  作者：William S. Emerson、Gail H. Birum、Raymond I. Longley

  DOI：10.1021/ja01102a013

  日期：1953.3
• Sancio; Sancio, Rendiconti del Seminario della Facolta di Scienze dell'Universita di Cagliari, 1957, vol. 27, p. 97,100
  作者：Sancio、Sancio

  DOI：——

  日期：——
• Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro
  作者：Sze Wei Leong、Suet Lin Chia、Faridah Abas、Khatijah Yusoff

  DOI：10.1016/j.ejmech.2018.08.039

  日期：2018.9

  In the present study, a series of forty-five asymmetrical meta-methoxylated diarylpentanoids have been synthesized, characterized and evaluated for their in-vitro anti-cancer potential. Among the forty-five analogs, three compounds (20, 33 and 42) have been identified as lead compounds due to their excellent inhibition against five human cancer cell lines including SW620, A549, EJ28, HT1080 and MCF-7. Structure-activity relationship study on cytotoxicity of tested compounds suggested that the presence of meta-oxygenated phenyl ring played a critical role in enhancing their cytotoxic effects. Compounds 33 and 42 in particular, exhibited strongest cytotoxicity against tested cell lines with the IC50 values ranging from 1.1 to 4.3 M. Subsequent colony formation assay on SW620 cell line showed that both compounds 33 and 42 possessed strong anti-proliferative activity. In addition, flow cytometry based experiments revealed that these compounds could trigger intracellular ROS production thus inducing G2/M-phase cell arrest and apoptosis. All these results suggested that poly meta-oxygenated diarylpentnoid is a promising scaffold which deserved further modification and investigation in the development of natural product based anti-cancer drug. (C) 2018 Elsevier Masson SAS. All rights reserved.