(E)-1,1-bis (methylthio)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one | 117672-15-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1,1-bis (methylthio)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• 英文别名: (4E)-1,1-bis(methylsulfanyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 117672-15-8
• 化学式: C₁₆H₂₀O₄S₂
• 分子量: 340.464
• InChiKey: VIKBHHWTZRAGKX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1,1-bis (methylthio)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 在 sodium hydroxide 、 四氯化锡 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 2-bis(methylthio)methylene-3-(3,4,5-trimethoxyphenyl)cyclopentanone
  参考文献：
  名称：

  Deb, Biswajit; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar, Journal of Chemical Research, Miniprint, 1990, # 11, p. 2728 - 2758

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-bis(methylthio)but-3-en-2-one 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以88%的产率得到(E)-1,1-bis (methylthio)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Convenient one-pot multicomponent strategy for the synthesis of 6-pyrrolylpyrimidines

  摘要：

  一种从α-芳香基丙烯酮二硫代乙醛2中以多组分方式构建二杂芳基的简便方法。反应在高的化学/位置选择性下进行，通过将2与对甲苯磺酰基)甲基异氰酸酯3（TosMIC）、硝酸胍酸盐5和醇在NaH/THF存在下进行环加成反应，高产率地生成4-烷氧基-6-(4-芳基-1H-吡咯-3-基)嘧啶-2-胺。

  DOI：

  10.1039/c4ra02891k

文献信息

• Synthesis of Methyl 5-Aryl-3-oxo-4-pentenoates and Novel Substituted Cyclopentenones
  作者：C. V. Asokan、S. Bhattacharji、H. Ila、H. Junjappa

  DOI：10.1055/s-1988-27543

  日期：——

  The cinnamoyl- (1a-j) and (5-phenyl-2,4-pentadienoyl)- (1k) ketene dithioacetals are shown to undergo methanolysis in the presence of ether-boron trifluoride complex and mercury(II) chloride to the corresponding methyl 5-aryl-3-oxo-4-pentenoates 2a-j and 3-oxo-7-phenyl- 4,6-heptadienoate (2k), respectively, in good yields. However, the corresponding (2-methylcinnamoyl)ketene dithioacetals 3a-f, under identical reaction conditions, undergo Nazarov cyclization to give the corresponding substituted cyclopentenones 4a-f.

  香豆醯基(1a-j)和(5-苯基-2,4-戊二烯酰基)(1k)酮烯二硫乙酰醇在醚-三氟化硼复合物和氯化汞存在下进行甲醇解，得到相应的甲基5-芳基-3-氧-4-戊烯酸酯2a-j和3-氧-7-苯基-4,6-庚二烯酸酯(2k)，产率良好。然而，相应的(2-甲基香豆醯基)酮烯二硫乙酰醇3a-f在相同反应条件下发生纳扎罗夫环化反应，生成相应的取代环戊烯酮4a-f。
• Cycloaromatization of α-Oxoketene Dithioacetals with 5-Lithiomethyl-3-methylisoxazole: A New General Method for the Synthesis of Substituted and Annulated 1,2-Benzisoxazoles
  作者：Dinah Pooranchand、J. Satyanarayana、H. Ila、H. Junjappa

  DOI：10.1055/s-1993-25840

  日期：——

  A new route to 6-substituted 4a-e and 5,6-annulated 4f-l 1,2-benzisoxazoles has been developed through regioselective 1,2-nucleophilic addition of 5-lithiomethyl-3-methylisoxazole (2) to a variety of α-oxoketene dithioacetals 1a-l and subsequent cycloaromatization of the resulting hydroxyacetals in the presence of boron trifluoride -diethyl ether complex. The corresponding 4-dethiomethylated benzisoxazoles 6a-d were also synthesized by cyclocondensation of β- methylthio-α,β-unsaturated ketones with 2 under identical conditions. The reaction was further extended for the synthesis of (6-benzisoxazolyl)-substituted ethylenes 9a-e, butadienes 9f-g and hexatriene 9h by subjecting α-cinnamoyl ketene dithioacetals 7a-e and their higher enyl analogs 7f-h to similar transformations.

  通过将 5-硫代甲基-3-甲基异噁唑（2）与多种δ-±-氧代酮二硫代乙醛 1a-l 进行 1,2-亲核加成，并随后在三氟化硼-二乙基醚络合物存在下对所生成的羟基乙醛进行环芳基化，开发出了一条制备 6-取代型 4a-e 和 5,6-annulated 4f-l 1,2-苯并异噁唑的新途径。在相同的条件下，δ-甲硫基-δ,δ-不饱和酮与 2 环缩合，也合成了相应的 4-二硫甲基化苯并异噁唑 6a-d。通过使δ-肉桂酰基酮二硫代乙醛 7a-e 及其高烯基类似物 7f-h 发生类似的转化，该反应进一步扩展到合成（6-苯并异噁唑基）取代的乙烯 9a-e、丁二烯 9f-g 和己三烯 9h。
• Polarized Ketene Dithioacetals; 55:¹Synthesis of Novel 5-Aryl-2-methylthio-4<i>H</i>-pyran-4-ones from Cinnamoylketene Dithioacetals
  作者：B. Deb、C. V. Asokan、H. Ila、H. Junjappa

  DOI：10.1055/s-1987-28112

  日期：——

  A novel method for the synthesis of 5-aryl-2-methylthio-4H-pyran-4-ones 4a-h has been developed from the corresponding cinnamoylketene dithioacetals 1a-h in three successive steps. In the first step, 1a-h were oxidized with alkaline hydrogen peroxide to give the corresponding (β-aryl-,α,β-epoxypropanoyl)ketene dithioacetals 2a-h in 78-89% overall yields. In the second step the epoxyketones 2a-h were subjected to rearrangement in the presence of ether-boron trifluoride complex to give the corresponding (α-formyl-α-phenylacetyl)ketene dithioacetals 3a-h, which were then cyclized in the third step by refluxing in acetic acid/ethanol to afford the title compounds in good yields.

  从相应的肉桂烯酮二硫代乙醛 1a-h 开始，分三个步骤合成了 5-芳基-2-甲硫基-4H-吡喃-4-酮 4a-h 的新方法。 第一步，用碱性过氧化氢氧化 1a-h，得到相应的（δ-芳基-,δ±,δ-环氧丙酰基）烯酮二硫代乙醛 2a-h，总产率为 78-89%。在第二步中，环氧酮 2a-h 在醚-三氟化硼络合物存在下进行重排，得到相应的（δ-甲酰基-δ-苯乙酰基）烯酮二硫代乙醛 3a-h，然后在第三步中通过在醋酸/乙醇中回流环化，以良好的收率得到标题化合物。
• Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents
  作者：S.N. Suryawanshi、Santosh Kumar、Rahul Shivahare、Susmita Pandey、Avinash Tiwari、Suman Gupta

  DOI：10.1016/j.bmcl.2013.06.060

  日期：2013.9

  A series of substituted aryl pyrimidine derivatives was synthesized and evaluated in vitro for their antileishmanial potential against intracellular amastigotes of Leishmania donovani using reporter gene luciferase assay. Among all, 8 compounds showed promising IC50 values ranging from 0.5 to 12.9 mu M. Selectivity indices (S.I.) of all these compounds are far better than reference drugs, sodium stibogluconate (SSG) and miltefosine. On the basis of good S.I., compounds were further screened for their in vivo antileishmanial activity against L. donovani/hamster model. Compounds 2d, 4a and 4b have shown significant inhibition of parasitic multiplication that is 88.4%, 78.1% and 78.2%, respectively at a daily dose of 50 mg/kg x 5 days, when administered intraperitoneally. Compound 2d is most promising one, which may provide a new lead that could be exploited as a new antileishmanial agent. (C) 2013 Elsevier Ltd. All rights reserved.
• Chemotherapy of leishmaniasis part II: synthesis and bioevaluation of substituted arylketene dithioacetals as antileishmanial agents
  作者：Susmita Pandey、S.N. Suryawanshi、Suman Gupta、V.M.L. Srivastava

  DOI：10.1016/j.ejmech.2005.02.007

  日期：2005.8

  Some novel aryl substituted ketene dithioacetals 6 (a-d), 9 (a-c) and 10 (a-c) have been synthesized using novel synthetic methods. The compounds were screened against Leishmania donovani in hamsters for their activity profile. Some of the compounds inhibited 50-65% parasite growth at 50 mg kg(-1) x 5 days. (c) 2005 Elsevier SAS. All rights reserved.