4'-(trifluoromethyl)spiro-4'-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丁烷
• 英文名称: 4'-(trifluoromethyl)spiro-4'-ol
• 英文别名: 2'-(Trifluoromethyl)spiro[adamantane-2,4'-thietane]-2'-ol
• 化学式: C₁₃H₁₇F₃OS
• 分子量: 278.339
• InChiKey: UKWOBCGYJDIMIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-(trifluoromethyl)spiro-4'-ol 在 双氧水 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以92%的产率得到3'-(trifluoromethyl)spiro[adamantane-2,1'-propane-1,'3'-sultin]-3'-ol
  参考文献：
  名称：

  Synthesis of CF₃-Containing Sulfur Heterocycles. The First Stable 2-Thietanol Derivative

  摘要：

  The reaction of a,P-unsaturated CF3-containing ketones R(1)R(2)C=CHCOCF3 1-4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5-8, or mercaptan, 9, were obtained. The reaction of 3-adamantylidene-1,1,1-trifluoropropan-2-one,3, results in the corresponding four-membered heterocycle 8, which has a stable 2-thietanol fragment. The oxidation of sulfides 5-8 by hydrogen peroxide yields sulfones 10-12 or 1,3-sultine 13 (in the case of 8). Product stereochemistry and reaction mechanism are discussed.

  DOI：

  10.1021/jo951351c
• 作为产物：
  描述：

  3-Adamantan-2-ylidene-1,1,1-trifluoro-propan-2-one 在 硫化氢铵 作用下， 以 乙醇 、 水 为溶剂， 反应 30.0h， 以86%的产率得到4'-(trifluoromethyl)spiro-4'-ol
  参考文献：
  名称：

  Synthesis of CF₃-Containing Sulfur Heterocycles. The First Stable 2-Thietanol Derivative

  摘要：

  The reaction of a,P-unsaturated CF3-containing ketones R(1)R(2)C=CHCOCF3 1-4 with ammonium hydrosulfide was investigated. The structure of the enones was shown to influence the reaction path, and the corresponding six-membered sulfur heterocycles bearing trifluoromethyl groups, 5-8, or mercaptan, 9, were obtained. The reaction of 3-adamantylidene-1,1,1-trifluoropropan-2-one,3, results in the corresponding four-membered heterocycle 8, which has a stable 2-thietanol fragment. The oxidation of sulfides 5-8 by hydrogen peroxide yields sulfones 10-12 or 1,3-sultine 13 (in the case of 8). Product stereochemistry and reaction mechanism are discussed.

  DOI：

  10.1021/jo951351c