8,8-diphenyl-7,9-dithiabicyclo[4.3.0]nonane

• 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: 8,8-diphenyl-7,9-dithiabicyclo[4.3.0]nonane
• 英文别名: (3aR,7aR)-2,2-diphenyl-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3]dithiole
• 化学式: C₁₉H₂₀S₂
• 分子量: 312.5
• InChiKey: GDKIPQDAUMAJGO-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化环己烯 、 二苯基甲烷硫酮 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以5.4%的产率得到trans-8,8-diphenyl-7,9-dioxabicyclo<4.3.0>nonane
  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

文献信息

• Lewis Acid Catalyzed Reactions of Thioketones with 1,2-Epoxycyclohexane and 1,2-Epoxycyclopentane
  作者：Milen Blagoev、Anthony Linden、Heinz Heimgartner

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

  日期：1999.12.15

  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).