(RS,SR)-2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (RS,SR)-2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol
• 英文别名: trans-2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol；(2R,3S)-2,3-bis(trifluoromethyl)-3,4-dihydro-1,4-benzothiazin-2-ol
• 化学式: C₁₀H₇F₆NOS
• 分子量: 303.228
• InChiKey: ANLVYOVKAGWEMM-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.6
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3-bis(trifluoromethyl)-2H-1,4-benzoxazin-2-ol 、 2-氨基苯硫醇 以 甲醇 为溶剂， 反应 36.0h， 生成 (RR,SS)-2,3-bis-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 、 (RS,SR)-2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol
  参考文献：
  名称：

  2,3-环氧八氟丁烷与2-氨基苯硫醇的反应

  摘要：

  The reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol in N,N-dimethylacetamide gave 3-(2-aminophenylsulfanyl)-1,1,1,3,4,4,4-heptafluorobutane-2,2-diol. In the reaction of the same compounds in dioxane, 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol was formed as a result of primary attack by the amino group in 2-aminobenzenethiol on the epoxy ring. The same product was obtained by treatment with 2-aminobenzenethiol of 2,3-bis(trifluoromethyl)-2H-1,4-benzoxazin-2-ol which was synthesized from 2,3-epoxyoctafluorobutane and 2-aminophenol.

  DOI：

  10.1134/s1070428006090090

文献信息

• A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane
  作者：Lyudmila V. Saloutina、Aleksandr Ya. Zapevalov、Victor I. Saloutin、Pavel A. Slepukhin、Mikhail I. Kodess、Valentina E. Kirichenko、Marina G. Pervova、Oleg N. Chupakhin

  DOI：10.1016/j.jfluchem.2007.04.006

  日期：2007.7

  The reaction of octafluoro-2,3-epoxybutane I with 2-aminothiophenol gave three kinds of novel fluorocontaining N,S-heterocyclic compounds depending on the solvent nature: 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 2, 2-trifluoromethyl-2-[1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-benzothiazolidine 6 and 5a,11a-bis(trifluoromethyl)-5a,6,11a,12-tetrahydro-5,11-dithia-6,12-diazanaphthacene 5. Use of the toluene, dioxane, tetrahydrofuran, acetonitrile and dimethoxyethane gave the unexpected dihydrobenzothiazine 2 (RS,SR > RR,SS) in good to moderate yields. In dimethylsulfoxide and N,N-dimethylacetamide, unusual cyclization occurred resulting in benzothiazolidine 6 (RS,SR/RR,SS similar to 1:1) in moderate yields. Formation of minor 1,1,1,3,4,4,4-heptafluoro-3-(2-aminophenylthio)-2,2-dihydroxybutane 4 which was converted into bis(benzothiazine) 5 was observed in all solvents tested with the exception of toluene and dioxane. The molecular structure of the RS,SR-diastereomer of dihydrobenzothiazine 2, bis(benzothiazine) 5 and the RS,SR-diastereomer of benzothiazolidine 6 has been established by X-ray crystallography. (c) 2007 Elsevier B.V. All rights reserved.