5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione | 73964-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione
• 英文别名: (+/-)-5-methylthiotetronic acid；5-methylthiotetronic acid；5-Methylthiolane-2,4-dione
• CAS: 73964-90-6
• 化学式: C₅H₆O₂S
• 分子量: 130.167
• InChiKey: NMOITQIHWFRQNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione 在 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 72.5h， 生成 3-[1-(allylamino)ethylidene]-5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione
  参考文献：
  名称：

  摘要：

  Acylation of (3H,5H)-tetrahydrothiophene-2,4-dione (thiotetronic acid) with acetyl, propionyl, and valeryl chlorides followed by O-C isomerization in the presence of 4-dimethylaminopyridine or acetone cyanohydrin gave rise to 3-acetyl, 3-propanoyl, and 3-pentanoyl derivatives of thiotetronic acid. The reaction of 3-acylthiotetronic acids with diazomethane afforded enol methyl ethers at the endocyclic keto groups. The subsequent reaction of these enol ethers with allylamine, benzylamine, and p-anisidine occurs along the mechanism of vinylog substitution providing the corresponding endocyclic enamino derivatives.

  DOI：

  10.1023/a:1013464314542
• 作为产物：
  描述：

  3-ethoxycarbonyl-5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione 在 三氟乙酸 作用下， 以95%的产率得到5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione
  参考文献：
  名称：

  摘要：

  Acylation of (3H,5H)-tetrahydrothiophene-2,4-dione (thiotetronic acid) with acetyl, propionyl, and valeryl chlorides followed by O-C isomerization in the presence of 4-dimethylaminopyridine or acetone cyanohydrin gave rise to 3-acetyl, 3-propanoyl, and 3-pentanoyl derivatives of thiotetronic acid. The reaction of 3-acylthiotetronic acids with diazomethane afforded enol methyl ethers at the endocyclic keto groups. The subsequent reaction of these enol ethers with allylamine, benzylamine, and p-anisidine occurs along the mechanism of vinylog substitution providing the corresponding endocyclic enamino derivatives.

  DOI：

  10.1023/a:1013464314542

文献信息

• Structure-Activity Relationships of Precursors and Analogs of Natural 3-Enoyl-tetramic Acids
  作者：Bertram Barnickel、Frances Bayliffe、Randi Diestel、Karl Kempf、Sabine Laschat、Steffen Pachali、Florenz Sasse、Andrea Schlenk、Rainer Schobert

  DOI：10.1002/cbdv.201000179

  日期：2010.12

  β-hydroxy-octatrienoyl amide precursor to aburatubolactam also exhibited distinct activity with an IC₅₀ (120 h) value of <2.5 μM. The length of 3-oligoenoyl residues had little influence on the anticancer activity, but 3-alka-oligoenoyl tetramic acids were far more efficacious than their 3-(4-methoxycinnamoyl) congeners. N-H-3-acyltetramic acids were generally more active than their N-Me or N-Boc analogs, unless further

  制备的片段和合成前体与大环3-酰基四酸（= 3-酰基-1,5-二氢-4-羟基-2H-吡咯-2-酮）烟酰胺内酰胺和大环蛋白A以及其他类似物在环杂原子（N，O，S）中的残基（N，O，S）和N（1），C（3）和C（5）处的残基进行了细胞毒性和抗菌作用测试。在体外针对各种肿瘤细胞系的抗癌活性不一定需要完整的吡咯烷-2,4-二酮环。环丁草内酰胺的无环β-羟基-八碳三烯酰基酰胺前体也表现出独特的活性，IC 50（120 h）值<2.5μM。3-寡烯酰基残基的长度对抗癌活性几乎没有影响，但是3-碱-寡烯酰基四酸比其3-（4-甲氧基肉桂酰基）同类物更有效。NH-3-酰基丁二酸通常比其N-Me或N-Boc类似物更具活性，除非另外的极性基团需要增加亲脂性以充分摄取。与同等取代的四酸相比，Tetronic和thiotetronic酸在癌细胞中的抗增殖能力要低得多。
• Diversity in the Base-induced Photoreactions of Thiolane-2,4-dione and Derivatives. Reductive Ring Cleavage and Novel Rearrangements of the Carbon Skeleton
  作者：Kimitoshi Saito、Tadashi Sato

  DOI：10.1246/bcsj.52.3601

  日期：1979.12

  The irradiation of thiolane-2,4-dione (thiotetronic acid) and its derivatives, 1a–1d, in methanol in the presence of bases induced the reductive ring cleavage to give β,β′-diketo esters. The base-induced reductive ring cleavage was also observed in aprotic solvents, such as acetonitrile or acetone, although the products were obtained as β,β′-diketo amides in these cases. On the other hand, the irradiation

  在碱存在的情况下，在甲醇中对硫戊环-2,4-二酮（硫代特酮酸）及其衍生物 1a-1d 进行辐照诱导还原性环裂解，生成 β,β'-二酮酯。在非质子溶剂（如乙腈或丙酮）中也观察到碱诱导的还原环裂解，尽管在这些情况下获得的产物是 β,β'-二酮酰胺。另一方面，在碱存在的情况下，在水中照射 1a-1d 会引起碳骨架的重排，生成琥珀酸硫酐、γ-酮酰胺或琥珀酰胺以及还原产物。当吡啶用作水中光解的碱时，两种 3-乙酰基衍生物 1a 和 1b 产生 γ-酮硫醇和相应的二硫化物，这是由另一种类型的碳骨架重排产生的。
• SAITO KIMITOSHI; SATO TADASHI, BULL. CHEM. SOC. JAP., 1979, 52, NO 12, 3601-3605,
  作者：SAITO KIMITOSHI、 SATO TADASHI

  DOI：——

  日期：——
• ——
  作者：M. V. Budnikova、D. B. Rubinov

  DOI：10.1023/a:1013464314542

  日期：——

  Acylation of (3H,5H)-tetrahydrothiophene-2,4-dione (thiotetronic acid) with acetyl, propionyl, and valeryl chlorides followed by O-C isomerization in the presence of 4-dimethylaminopyridine or acetone cyanohydrin gave rise to 3-acetyl, 3-propanoyl, and 3-pentanoyl derivatives of thiotetronic acid. The reaction of 3-acylthiotetronic acids with diazomethane afforded enol methyl ethers at the endocyclic keto groups. The subsequent reaction of these enol ethers with allylamine, benzylamine, and p-anisidine occurs along the mechanism of vinylog substitution providing the corresponding endocyclic enamino derivatives.