(E)-5-Benzo[1,3]dioxol-5-yl-1,1-bis-methylsulfanyl-penta-1,4-dien-3-one | 89812-54-4

• 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-Benzo[1,3]dioxol-5-yl-1,1-bis-methylsulfanyl-penta-1,4-dien-3-one
• 英文别名: (4E)-5-(1,3-benzodioxol-5-yl)-1,1-bis(methylsulfanyl)penta-1,4-dien-3-one
• CAS: 89812-54-4
• 化学式: C₁₄H₁₄O₃S₂
• 分子量: 294.395
• InChiKey: DKBMTUPDYWZPMP-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-Benzo[1,3]dioxol-5-yl-1,1-bis-methylsulfanyl-penta-1,4-dien-3-one 在 sodium hydroxide 、 甲酸 、 磷酸 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-(3,4-methylenedioxyphenyl)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：

  胡椒醛 、 4,4-bis(methylthio)but-3-en-2-one 生成 (E)-5-Benzo[1,3]dioxol-5-yl-1,1-bis-methylsulfanyl-penta-1,4-dien-3-one
  参考文献：
  名称：

  MYRBOH, B.;ASOKAN, C. V.;ILA, H.;JUNJAPPA, H., SYNTHESIS, BRD, 1984, N 1, 50-51

  摘要：

  DOI：

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。
• 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。
• Singh, L. W.; Ila, H.; Junjappa, H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 607 - 610
  作者：Singh, L. W.、Ila, H.、Junjappa, H.

  DOI：——

  日期：——