diethyl 2-(2-acetylmercapto)benzoylmalonate | 273380-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 2-(2-acetylmercapto)benzoylmalonate
• 英文别名: Diethyl 2-(2-acetylsulfanylbenzoyl)propanedioate
• CAS: 273380-14-6
• 化学式: C₁₆H₁₈O₆S
• 分子量: 338.381
• InChiKey: PGDKRVWDPFRYSO-UHFFFAOYSA-N

物化性质

• 沸点：
  422.7±35.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-acetylmercapto)benzoylmalonate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-hydroxythiochromen-4-one
  参考文献：
  名称：

  Synthesis and characterization of an anticoagulant 4-hydroxy-1-thiocoumarin by FTIR, FT-Raman, NMR, DFT, NBO and HOMO–LUMO analysis

  摘要：

  Experimental and theoretical investigations on the molecular structural, electronic and the vibrational characteristics of 4-hydroxy-1-thiocoumarin are presented. Conformational analysis was carried out to obtain the more stable configuration of the compound. The vibrational frequencies were obtained by DFT/B3LYP calculations employing 6-311++G(d,p), 6-31G(d,p), cc-pVTZ basic sets and B3PW91 method with 6-311++G(d,p) basis set and are compared with FTIR and FT-Raman spectral data recorded in the region of 4000-400 and 4000-100 cm(-1), respectively. The total electron density and molecular electrostatic potential surfaces of the molecule were constructed to display electrostatic potential (electron + nuclei) distribution. The electronic properties HOMO and LUMO energies were measured. H-1 and C-13 NMR spectra were recorded and H-1 and C-13 nuclear magnetic resonance chemical shifts of the molecule were calculated by using the Gauge-Independent Atomic Orbital (GIAO) method and analyzed. The picture of localized bonds and lone pairs, stabilization energy of the delocalization of electrons, the charge and hybridisation of the atoms of 4-hydroxy-1-thiocoumarin were clearly explained by NBO analysis. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.01.014
• 作为产物：
  描述：

  2-(乙酰基硫代)苯甲酸 在 氯化亚砜 、 乙醇 、 magnesium 、 尿素 作用下， 以 四氯化碳 、 乙醚 、 甲苯 为溶剂， 反应 7.0h， 生成 diethyl 2-(2-acetylmercapto)benzoylmalonate
  参考文献：
  名称：

  Efficient and Practical Syntheses of Benzothiopyran Derivatives

  摘要：

  Concise and inexpensive methods for the preparation of 4-hydroxy-1-thiocoumarin and 2-methylthiochromone from 2-mercaptobenzoic acid are described, which should be readily amenable to large scale synthesis.

  DOI：

  10.1080/00397910008087139

文献信息

• Efficient and Practical Syntheses of Benzothiopyran Derivatives
  作者：Jae-Chul Jung、Ju-Cheun Kim、Oee-Sook Park

  DOI：10.1080/00397910008087139

  日期：2000.4

  Concise and inexpensive methods for the preparation of 4-hydroxy-1-thiocoumarin and 2-methylthiochromone from 2-mercaptobenzoic acid are described, which should be readily amenable to large scale synthesis.
• Synthesis and characterization of an anticoagulant 4-hydroxy-1-thiocoumarin by FTIR, FT-Raman, NMR, DFT, NBO and HOMO–LUMO analysis
  作者：V. Arjunan、R. Santhanam、S. Sakiladevi、M.K. Marchewka、S. Mohan

  DOI：10.1016/j.molstruc.2013.01.014

  日期：2013.4

  Experimental and theoretical investigations on the molecular structural, electronic and the vibrational characteristics of 4-hydroxy-1-thiocoumarin are presented. Conformational analysis was carried out to obtain the more stable configuration of the compound. The vibrational frequencies were obtained by DFT/B3LYP calculations employing 6-311++G(d,p), 6-31G(d,p), cc-pVTZ basic sets and B3PW91 method with 6-311++G(d,p) basis set and are compared with FTIR and FT-Raman spectral data recorded in the region of 4000-400 and 4000-100 cm(-1), respectively. The total electron density and molecular electrostatic potential surfaces of the molecule were constructed to display electrostatic potential (electron + nuclei) distribution. The electronic properties HOMO and LUMO energies were measured. H-1 and C-13 NMR spectra were recorded and H-1 and C-13 nuclear magnetic resonance chemical shifts of the molecule were calculated by using the Gauge-Independent Atomic Orbital (GIAO) method and analyzed. The picture of localized bonds and lone pairs, stabilization energy of the delocalization of electrons, the charge and hybridisation of the atoms of 4-hydroxy-1-thiocoumarin were clearly explained by NBO analysis. (C) 2013 Elsevier B.V. All rights reserved.