spiro[7,9-dithiabicyclo[4.3.0]nonane-8,9'-[9H]xanthene]

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro[7,9-dithiabicyclo[4.3.0]nonane-8,9'-[9H]xanthene]
• 英文别名: (3aR,7aR)-spiro[3a,4,5,6,7,7a-hexahydrobenzo[d][1,3]dithiole-2,9'-xanthene]
• 化学式: C₁₉H₁₈OS₂
• 分子量: 326.483
• InChiKey: BUJUNNUCZXMJRV-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-噻吨酮 、 氧化环己烯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以5.39%的产率得到spiro[7,9-dithiabicyclo[4.3.0]nonane-8,9'-[9H]xanthene]
  参考文献：
  名称：

  Lewis Acid Catalyzed Reactions of Thioketones with 1,2-Epoxycyclohexane and 1,2-Epoxycyclopentane

  摘要：

  Non-enolizable thioketones and 1,2-epoxycycloalkanes undergo a Lewis acid catalyzed addition reaction to give 1.3-oxathiolanes. Appropriate reaction conditions are CH2Cl2 as the solvent, BF3. Et2O as the Lewis acid, and a temperature between -78 degrees and r.t. Under the reaction conditions, the 1,3-oxathiolanes are only moderately stable. They decompose to yield the corresponding epithiocycloalkane and ketone. In general, 1,3-dithiolanes are isolated as minor products or, after prolonged reaction, as the main product. These secondary products are formed via the Lewis acid catalyzed reaction of the intermediate epithiocycloalkane and a second molecule of the thioketone. In the reaction of thiobenzophenone and 1.2-epoxycyclohexane, trans-8,8-diphenyl-7,9-dioxabicyclo[4.3.0]nonane is formed in small amounts as an additional side product (Scheme 12). in all cases, the newly formed heterocycle and the carbocycle are trans-fused. This result is consistent with a nucleophilic ring-opening of the complexed oxirane by the thioketone via inversion of the configuration and subsequent formation of the O(1)-C(2) bond of the 13-oxathiolane (Scheme 13). The surprising formation of the fused 1,4-oxathiepan derivative 23 (Scheme 9) is in accordance with un ionic reaction mechanism (cf. Scheme 15).

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2316::aid-hlca2316>3.0.co;2-3