3,4-dimercapto-benzene-1,2-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4-dimercapto-benzene-1,2-diol
• 英文别名: Dimercaptocatechol；3,4-bis(sulfanyl)benzene-1,2-diol
• 化学式: C₆H₆O₂S₂
• 分子量: 174.244
• InChiKey: UIUMXCQKGIFORB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-苯醌 在 H₂S(x) 作用下， 生成 3,4-dimercapto-benzene-1,2-diol
  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

文献信息

• Regioselective (Biomimetic) Synthesis of a Pentasulfane from <i>ortho</i>-Benzoquinone
  作者：David Aebisher、Edyta M. Brzostowska、Adaickapillai Mahendran、Alexander Greer

  DOI：10.1021/jo062677w

  日期：2007.4.1

  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.