acetic acid 2-acetoxy-5-acetylsulfanyl-phenyl ester | 27320-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: acetic acid 2-acetoxy-5-acetylsulfanyl-phenyl ester
• 英文别名: ethanethioic acid, S-[3,4-bis(acetyloxy)phenyl] ester；(2-acetyloxy-4-acetylsulfanylphenyl) acetate
• CAS: 27320-23-6
• 化学式: C₁₂H₁₂O₅S
• 分子量: 268.29
• InChiKey: RKXULWPQBTWZNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-苯醌 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以0.0048 g的产率得到acetic acid 2-acetoxy-3-(2,3-diacetoxy-phenyldisulfanyl)-phenyl ester
  参考文献：
  名称：

  Regioselective (Biomimetic) Synthesis of a Pentasulfane from ortho-Benzoquinone

  摘要：

  A mechanism is proposed for the formation of cyclic 5,6,7,8,9-pentathiabenzocycloheptene-1,2-diol, 4, from the reaction of o-benzoquinone with reduced elemental sulfur, H2Sx. 1,6-Conjugate addition to the quinone is favored over 1,4-conjugate addition. Hydrogen bonding to the quinone oxygen enhances the nucleophilicity of H2Sx by facilitating the removal of the S-H proton. We propose that initially formed 3-polysulfidobenzene-diol intermediates are oxidized to their corresponding quinones and closure of the polysulfur ring subsequently takes place at the C3-C4 bond leading to 4. A possible mechanism for the formation of the pentasulfur linkage in 4 is discussed, which is the key moiety found in a number of natural products.

  DOI：

  10.1021/jo062677w