2-(1,3-Dithiolan-2-ylidene)-5-(4-methoxyphenyl)-3-oxopent-4-enoic acid | 133286-20-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-(1,3-Dithiolan-2-ylidene)-5-(4-methoxyphenyl)-3-oxopent-4-enoic acid
• CAS: 133286-20-1
• 化学式: C₁₅H₁₄O₄S₂
• 分子量: 322.406
• InChiKey: CIGHLURBFNHDGV-UHFFFAOYSA-N

物化性质

• 沸点：
  518.5±50.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dithiolan-2-ylidene)-5-(4-methoxyphenyl)-3-oxopent-4-enoic acid 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到4-chloro-3-(1,3-dithiolan-2-ylidene)-6-(4-methoxyphenyl)-3,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Direct Synthesis of Polyfunctionalized Unsaturated δ-Lactones and δ-Lactams from α-Alkenoyl α-Carboxyl/Carbamoyl Ketene S,S-Acetals under Vilsmeier Conditions

  摘要：

  An efficient method for direct synthesis of polyfunctionalized unsaturated delta-lactones 2 and delta-lactams 4 has been developed from the reaction of the easily available alpha-alkenoyl alpha-carboxy/carbamoyl ketene S,S-acetals 1/3 and Vilsmeier reagents (DMF/POCl3 or DMF/PBr3) via a cyclization followed by a halovinylation or haloformylation sequence.

  DOI：

  10.1021/jo900663z

文献信息

• Syntheses and Characterization of Tributyltin(IV) Carboxylates Containing α‐Oxoketene Cyclic Dithioacetals
  作者：Fushun Liang、Jianxin Li、Qun Liu、Yan Xing、Hengqing Jia、Ninghai Hu、Yonghua Lin

  DOI：10.1081/sim-120019995

  日期：2003.1.6

  Five aquatributyltin-2-(dialkylthio)methylene-3-oxo-5-aryl-4-pentenoates (3) were synthesized and characterized by IR spectra, H-1 NMR spectra, C-13 NMR spectra and elemental analyses. The IR spectra of (3) show strong O-H stretching modes in the region of 3384-3455 cm(-1). In the H-1 NMR spectra of (3), signals due to the protons of an alpha-oxoketene dithioacetal segment shift upfield compared to those of free acids (2). This is indicative of the formation of the tin ester complexes. The structure of 4-O2N-C6H4CH=CHCOC(C3H4S2)CO2Sn(C4H9)(3).(H2O) (3d) was determined by X-ray diffraction and showed two molecules in an asymmetric unit cell. The tin(IV) is coordinated with three carbon atoms, an oxygen of carboxylate and an oxygen of water and forms a five-coordinate, distorted trigonal bipyramidal configuration. There is no intermolecular O-Sn coordination in (3d), but a molecule of water acts as one of the five ligands and coordinates directly to the tin atom. The tin-oxygen (water) bond distance in (3d) is discussed in relation to that in other aquatin(IV) complexes.
• Direct Synthesis of Polyfunctionalized Unsaturated δ-Lactones and δ-Lactams from α-Alkenoyl α-Carboxyl/Carbamoyl Ketene <i>S</i>,<i>S</i>-Acetals under Vilsmeier Conditions
  作者：Jun Liu、Mang Wang、Feng Han、Yingjie Liu、Qun Liu

  DOI：10.1021/jo900663z

  日期：2009.7.17

  An efficient method for direct synthesis of polyfunctionalized unsaturated delta-lactones 2 and delta-lactams 4 has been developed from the reaction of the easily available alpha-alkenoyl alpha-carboxy/carbamoyl ketene S,S-acetals 1/3 and Vilsmeier reagents (DMF/POCl3 or DMF/PBr3) via a cyclization followed by a halovinylation or haloformylation sequence.