cis-3,7-Diphenyl-1,2-dithiepan-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-3,7-Diphenyl-1,2-dithiepan-5-one
• 英文别名: (3R,7S)-3,7-diphenyldithiepan-5-one
• 化学式: C₁₇H₁₆OS₂
• 分子量: 300.445
• InChiKey: QIBRNQNUMSJKKP-CALCHBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  联甲基苯乙烯酮 在 双十烷基二甲基溴化铵 (NH₄)2Sx 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 cis-3,7-Diphenyl-1,2-dithiepan-5-one 、 trans-3,7-Diphenyl-1,2-dithiepan-5-one 、 trans-2,6-Diphenyltetrahydrothiopyran-4-one
  参考文献：
  名称：

  Phase-transfer-catalyzed reactions between polysulfide anions and .alpha.,.beta.-unsaturated carbonyl compounds

  摘要：

  Ammonium polysulfide reacts with alpha,beta-unsaturated ketones and aldehydes under PTC (phase transfer catalysis) conditions in a rather different manner than it does in homogeneous systems. 1,3-Diphenyl-2-propen-1-one (chalcone, 1) and 4-phenyl-3-buten-2-one (benzylideneacetone, 3) give sulfur-linked dimers (mainly disulfides). 3-Phenyl-2-propen-1-al (cinnamaldehyde) polymerizes. 1,5-Diphenyl-1,4-pentadien-3-one (dibenzylideneacetone, 7) gives the known six-membered ring thianones and new seven-membered ring 1,2-dithiepanones 9 along with a polymer. Carvone gives a disulfide dimer that converts to a mixture of bicyclic sulfur-containing compounds. Sodium polysulfide is much less effective because of the base-induced decomposition of either the products or the intermediates. Sodium sulfide reacts in the same manner as it does in homogenous systems.

  DOI：

  10.1021/jo00074a043

文献信息

• Phase-transfer-catalyzed reactions between polysulfide anions and .alpha.,.beta.-unsaturated carbonyl compounds
  作者：Eitan B. Krein、Zeev Aizenshtat

  DOI：10.1021/jo00074a043

  日期：1993.10

  Ammonium polysulfide reacts with alpha,beta-unsaturated ketones and aldehydes under PTC (phase transfer catalysis) conditions in a rather different manner than it does in homogeneous systems. 1,3-Diphenyl-2-propen-1-one (chalcone, 1) and 4-phenyl-3-buten-2-one (benzylideneacetone, 3) give sulfur-linked dimers (mainly disulfides). 3-Phenyl-2-propen-1-al (cinnamaldehyde) polymerizes. 1,5-Diphenyl-1,4-pentadien-3-one (dibenzylideneacetone, 7) gives the known six-membered ring thianones and new seven-membered ring 1,2-dithiepanones 9 along with a polymer. Carvone gives a disulfide dimer that converts to a mixture of bicyclic sulfur-containing compounds. Sodium polysulfide is much less effective because of the base-induced decomposition of either the products or the intermediates. Sodium sulfide reacts in the same manner as it does in homogenous systems.