2,2'-[thiobis(methylene)]bis[1,1,1,3,3,3-hexafluoro-2-propanol] | 73117-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-[thiobis(methylene)]bis[1,1,1,3,3,3-hexafluoro-2-propanol]
• 英文别名: 1,1,1,3,3,3-hexafluoro-2-[[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]sulfanylmethyl]propan-2-ol
• CAS: 73117-02-9
• 化学式: C₈H₆F₁₂O₂S
• 分子量: 394.181
• InChiKey: XWLYNUCRQKLKFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2'-[thiobis(methylene)]bis[1,1,1,3,3,3-hexafluoro-2-propanol] 在 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 以51%的产率得到
  参考文献：
  名称：

  Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

  摘要：

  Reaction of 2-trifluoromethyl- (1) and 2,2-bis(trifluoromethyl)- (2) oxiranes with a variety of sulfur nucleophiles proceeds rapidly and under mild conditions. For example, epoxide 2 reacts with aqueous solution of Na(2)S, producing S[CH(2)C(CF(3))(2)OH](2). Reaction of 2 with Na(2)S(2)O(3) leads to the formation of the corresponding Bunte salt. Interaction of 2 with NaSCN in water proceeds exothermically and results in high-yield formation of cyclic imine 5. Although this material can be isolated, it has limited stability and undergoes cyclotrimerization at ambient temperature, giving the corresponding 1,3,5-triazine. A number of heterocyclic compounds containing pendant -CH(2)C(CF(3))(2)OH group were prepared by the reaction of the corresponding thio-derivatives, such as pyridine-2-thiole with epoxide 2. It was found that fluoride anion catalyzes the reaction of epoxides 1 and 2 with isothiocyanates carrying electron withdrawing groups at nitrogen. The reaction results in nucleophilic cyclization and formation of the corresponding exocyclic imines containing a 1,3-oxothiolane moiety. Carbon disulfide was also found to be active in this process, reacting with epoxides 1 and 2 at ambient to give the corresponding trifluoromethylated 1,3-oxathiolane-2-thiones in 58-65% yield. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.11.003
• 作为产物：
  描述：

  3,3,3,-三氟-2-(三氟甲基)-1,2-氧化丙烯 在 sodium sulfide 、 氯化铵 作用下， 以 水 为溶剂， 以66%的产率得到2,2'-[thiobis(methylene)]bis[1,1,1,3,3,3-hexafluoro-2-propanol]
  参考文献：
  名称：

  Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

  摘要：

  Reaction of 2-trifluoromethyl- (1) and 2,2-bis(trifluoromethyl)- (2) oxiranes with a variety of sulfur nucleophiles proceeds rapidly and under mild conditions. For example, epoxide 2 reacts with aqueous solution of Na(2)S, producing S[CH(2)C(CF(3))(2)OH](2). Reaction of 2 with Na(2)S(2)O(3) leads to the formation of the corresponding Bunte salt. Interaction of 2 with NaSCN in water proceeds exothermically and results in high-yield formation of cyclic imine 5. Although this material can be isolated, it has limited stability and undergoes cyclotrimerization at ambient temperature, giving the corresponding 1,3,5-triazine. A number of heterocyclic compounds containing pendant -CH(2)C(CF(3))(2)OH group were prepared by the reaction of the corresponding thio-derivatives, such as pyridine-2-thiole with epoxide 2. It was found that fluoride anion catalyzes the reaction of epoxides 1 and 2 with isothiocyanates carrying electron withdrawing groups at nitrogen. The reaction results in nucleophilic cyclization and formation of the corresponding exocyclic imines containing a 1,3-oxothiolane moiety. Carbon disulfide was also found to be active in this process, reacting with epoxides 1 and 2 at ambient to give the corresponding trifluoromethylated 1,3-oxathiolane-2-thiones in 58-65% yield. (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.11.003

文献信息

• Boeré, René T.; Brown, W. Mark; Stephan, Douglas W., Inorganic Chemistry, 1985, vol. 24, # 4, p. 593 - 597
  作者：Boeré, René T.、Brown, W. Mark、Stephan, Douglas W.、Willis, Christopher J.

  DOI：——

  日期：——
• MIR QUI-CHEE; SHREEVE J. M., INORG. CHEM., 1980, 19, NO 6, 1510-1514
  作者：MIR QUI-CHEE、 SHREEVE J. M.

  DOI：——

  日期：——