(E)-5-(3,4-dimethoxyphenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one | 117672-14-7

• 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)-5-(3,4-dimethoxyphenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one
• 英文别名: (4E)-5-(3,4-dimethoxyphenyl)-1,1-bis(methylsulfanyl)penta-1,4-dien-3-one
• CAS: 117672-14-7
• 化学式: C₁₅H₁₈O₃S₂
• 分子量: 310.438
• InChiKey: YKOHDPPHKSTQOE-FNORWQNLSA-N

物化性质

• 沸点：
  461.2±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-5-(3,4-dimethoxyphenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one 在 一水合肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 20.0h， 以80%的产率得到3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methylsulfanyl-1H-pyrazole
  参考文献：
  名称：

  Purkayastha, M. L.; Patro, B.; Ila, H., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1341 - 1350

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-bis(methylthio)but-3-en-2-one 、 3,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以89%的产率得到(E)-5-(3,4-dimethoxyphenyl)-1,1-bis(methylthio)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。
• Studies on lead tetraacetate oxidation of α-oxoketene dithioacetals
  作者：Laxminarayan Bhat、Abraham Thomas、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)80925-x

  日期：1991.1

  α-acylketene dithioacetals in refluxing benzene affords α-acetoxyketene dithioacetals as major products which could be hydrolyzed to α-diketone dithioacetals under mild alkaline conditions. Under similar oxidative conditions, α-cinnamoyl ketene dithioacetals yield 2-acetoxycyclopentenone derivatives through an interesting oxidative Nazarov cyclization involving intermediate α-acetoxy dithioacetals accompanied

  在回流的苯中，无环α-酰基乙烯酮二硫缩醛的四乙酸铅氧化得到α-乙酰氧基烯酮二硫缩醛作为主要产物，可以在温和的碱性条件下水解为α-二酮二硫缩醛。在相似的氧化条件下，α-肉桂酰基烯酮二硫缩醛通过有趣的氧化Nazarov环化反应生成2-乙酰氧基环戊烯酮衍生物，其中涉及中间α-乙酰氧基二硫缩醛并伴有1,2-酰基迁移。
• 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。
• Deb, Biswajit; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar, Journal of Chemical Research, Miniprint, 1990, # 11, p. 2728 - 2758
  作者：Deb, Biswajit、Ila, Hiriyakkanavar、Junjappa, Hiriyakkanavar

  DOI：——

  日期：——
• 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.