1,1,1,3,3,3-hexafluoro-2-(mercaptomethyl)propan-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1,3,3,3-hexafluoro-2-(mercaptomethyl)propan-2-ol
• 英文别名: 1,1,1,3,3,3-Hexafluoro-2-(sulfanylmethyl)propan-2-ol
• 化学式: C₄H₄F₆OS
• 分子量: 214.132
• InChiKey: WZXWKGDYYZTLKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,1,1,3,3,3-hexafluoro-2-(mercaptomethyl)propan-2-ol 、 3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole 在 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以29%的产率得到1,1,1,3,3,3-hexafluoro-2-(((5-fluoro-2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)pyrimidin-4-yl)thio)methyl)propan-2-ol
  参考文献：
  名称：

  [EN] sGC STIMULATORS
  [FR] STIMULATEURS DE SGC

  摘要：

  公开号：

  WO2016044445A3
• 作为产物：
  描述：

  3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl carbamimidothioate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以90%的产率得到1,1,1,3,3,3-hexafluoro-2-(mercaptomethyl)propan-2-ol
  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

• Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides
  作者：Viacheslav A. Petrov、Will Marshall

  DOI：10.1016/j.jfluchem.2010.11.003

  日期：2011.1

  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.
• [EN] sGC STIMULATORS<br/>[FR] STIMULATEURS DE SGC
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2016044445A3

  公开（公告）日：2016-05-19