3-acetyl-5-[(Z)-phenylmethylidene]tetrahydrothiophene-2,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-5-[(Z)-phenylmethylidene]tetrahydrothiophene-2,4-dione
• 英文别名: (5Z)-3-acetyl-5-benzylidenethiolane-2,4-dione
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: AXESDJCDBDUBMH-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-5-[(Z)-phenylmethylidene]tetrahydrothiophene-2,4-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到3-acetyl-5-benzyltetrahydrothiophene-2,4-dione
  参考文献：
  名称：

  Synthesis and antiphospholipase activity of 3,5-disubstituted thiotetronic acid derivatives

  摘要：

  The condensation of 3-acetyltetrahydrothiophene-2,4-dione with aromatic aldehydes in the presence of piperidine as a catalyst gave a series of 5-arylmethylidene-3-acetyltetrahydrothiophene-2,4-diones. The reaction with excess aldehyde (2.5 equiv) led to the formation of bis-condensation products, 5-arylmethylidene-3-(3-aryl-1-oxoprop-2-enyl)tetrahydrothiophene-2,4-diones. Analogous 3,5-disubstituted tetrahydrothiophene-2,4-dione derivatives with different aryl groups in the ring and the side chain were synthesized by two-step condensation with the use of differently substituted aromatic aldehydes. Catalytic hydrogenation of both mono- and bis-adducts resulted in the reduction of the side-chain double C=C bond. while ionic hydrogenation with triethylsilane in trifluoroacetic acid in the presence of lithium perchlorate involved both the double C=C bond and carbonyl group in the side chain. The isolated products showed an appreciable effect on the activity of two secretory phospholipases A(2) from various sources.

  DOI：

  10.1134/s1070428006030146
• 作为产物：
  描述：

  3-acetyl-(3H,5H)-tetrahydrothiophene-2,4-dione 、 苯甲醛 在 哌啶 作用下， 以 甲苯 为溶剂， 以82%的产率得到3-acetyl-5-[(Z)-phenylmethylidene]tetrahydrothiophene-2,4-dione
  参考文献：
  名称：

  Synthesis and antiphospholipase activity of 3,5-disubstituted thiotetronic acid derivatives

  摘要：

  The condensation of 3-acetyltetrahydrothiophene-2,4-dione with aromatic aldehydes in the presence of piperidine as a catalyst gave a series of 5-arylmethylidene-3-acetyltetrahydrothiophene-2,4-diones. The reaction with excess aldehyde (2.5 equiv) led to the formation of bis-condensation products, 5-arylmethylidene-3-(3-aryl-1-oxoprop-2-enyl)tetrahydrothiophene-2,4-diones. Analogous 3,5-disubstituted tetrahydrothiophene-2,4-dione derivatives with different aryl groups in the ring and the side chain were synthesized by two-step condensation with the use of differently substituted aromatic aldehydes. Catalytic hydrogenation of both mono- and bis-adducts resulted in the reduction of the side-chain double C=C bond. while ionic hydrogenation with triethylsilane in trifluoroacetic acid in the presence of lithium perchlorate involved both the double C=C bond and carbonyl group in the side chain. The isolated products showed an appreciable effect on the activity of two secretory phospholipases A(2) from various sources.

  DOI：

  10.1134/s1070428006030146

文献信息

• Synthesis and antiphospholipase activity of 3,5-disubstituted thiotetronic acid derivatives
  作者：D. B. Rubinov、T. A. Zheldakova、I. L. Rubinova、S. V. Kuchuro、S. V. Babitskaya、G. N. Rakhuba、N. M. Litvinko

  DOI：10.1134/s1070428006030146

  日期：2006.3

  The condensation of 3-acetyltetrahydrothiophene-2,4-dione with aromatic aldehydes in the presence of piperidine as a catalyst gave a series of 5-arylmethylidene-3-acetyltetrahydrothiophene-2,4-diones. The reaction with excess aldehyde (2.5 equiv) led to the formation of bis-condensation products, 5-arylmethylidene-3-(3-aryl-1-oxoprop-2-enyl)tetrahydrothiophene-2,4-diones. Analogous 3,5-disubstituted tetrahydrothiophene-2,4-dione derivatives with different aryl groups in the ring and the side chain were synthesized by two-step condensation with the use of differently substituted aromatic aldehydes. Catalytic hydrogenation of both mono- and bis-adducts resulted in the reduction of the side-chain double C=C bond. while ionic hydrogenation with triethylsilane in trifluoroacetic acid in the presence of lithium perchlorate involved both the double C=C bond and carbonyl group in the side chain. The isolated products showed an appreciable effect on the activity of two secretory phospholipases A(2) from various sources.