2-氨基-5-氟-3-甲基苯硫醇 | 211868-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 2-氨基-5-氟-3-甲基苯硫醇
• 英文名称: 5-fluoro-3-methyl-2-amino-benzenethiol
• 英文别名: 2-amino-5-fluoro-3-methylbenzenethiol
• CAS: 211868-21-2
• 化学式: C₇H₈FNS
• 分子量: 157.212
• InChiKey: CJVMGHHMHBIMHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-5-氟-3-甲基苯硫醇 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of 7-ethoxy- and 7-fluoro-phenothiazines

  摘要：

  Synthesis of 7-ethoxy- and 7-fluoro-phenothiazines is reported by Smiles rearrangement of 5-ethoxy- and 5-fluoro-2-formamido-2'nitrodiphenylsulfides. The later were obtained by the formylation of 2-amino-5-ethoxy/5-fluoro-2'-nitrodiphenylsulfides which were prepared by the condensation of 2-amino-5-ethoxyl-5-fluoro-benzenethiols with o-halonitrobenzenes.

  DOI：

  10.1080/714040982

文献信息

• Synthesis of fluorophenothiazines via Smiles rearrangement and their conversion into sulfones
  作者：Neerja Sharma、Rajni Gupta、Mahendra Kumar、R.R Gupta

  DOI：10.1016/s0022-1139(99)00098-6

  日期：1999.9

  The synthesis of 3-fluoro-1-methylphenothiazines and 7-fluoro-9-methylnitrophenothiazines is reported. 3-Fluoro-1-methylphenothiazines have been prepared by Smiles rearrangement of 5-fluoro-3-methyl-2-formamido-2-nitrodiphenyl sulfides in alcoholic potassium hydroxide solution. The formyl derivatives were prepared by the formylation of resultant diphenyl sulfides obtained by the condensation of 2-

  据报道3-氟-1-甲基吩噻嗪和7-氟-9-甲基硝基吩噻嗪的合成。3-氟-1-甲基吩噻嗪是通过将5-氟-3-甲基-2-甲酰胺基-2-硝基二苯硫醚在氢氧化钾醇溶液中进行Smiles重排而制备的。甲酰基衍生物是通过将2-氨基-5-氟-3-甲基苯硫醇与邻卤代硝基苯在乙酸钠乙醇溶液中缩合制得的所得二苯硫醚甲酰化而制得的。通过2-氨基-5-氟-3-甲基苯硫醇与邻氨基的缩合反应制得7-氟-9-甲基硝基吩噻嗪在原位发生Smiles重排的乙醇氢氧化钠溶液中，在与反应性卤原子相对的两个邻位上都含有硝基或一个硝基和卤原子的-卤代硝基苯。氟化砜是通过在冰醋酸中用30％过氧化氢氧化氟化吩噻嗪而合成的。
• Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide
  作者：J. E. Drake、M. B. Hursthouse、M. E. Light、R. Maheshwari、K. G. Ojha、R. Ratnani

  DOI：10.1007/s10870-008-9353-7

  日期：2008.7

  Bis(2-amino-5-fluoro-3-methylphenyl)disulfide was obtained by oxidation of 2-amino-5-fluoro-3-methylbenzenethiol and was characterized by elemental analysis, IR and 1H-NMR spectroscopy. The X-ray structure was determined. Crystal data: C14H14N2F2S2: Monoclinic, P21 /n, a = 11.8268(3), b = 9.5770(3), c = 12.3977(3) Å, β = 98.079(2)°, V = 1390.29(7) Å, Z = 4. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds. Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide J. E. Drake1, M. B. Hursthouse2, M. E. Light2, R. Maheshwari3, K.G. Ojha3, R. Ratnani3* Bis(2-amino-5-fluoro-3-methylphenyl)disulfide is linked into a three-dimensional frame work by a combination of intermolecular N–H···F and N–H···N and intramolecular N–H···S hydrogen bonds. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.

  双（2-氨基-5-氟-3-甲基苯基）二硫醚是通过氧化2-氨基-5-氟-3-甲基苯硫醇得到的，并通过元素分析、红外光谱和1H-NMR光谱进行了表征。X射线结构测定。晶体数据：C14H14N2F2S2：单斜晶系，P21/n，a=11.8268(3)，b=9.5770(3)，c=12.3977(3)Å，β=98.079(2)°，V=1390.29(7)Å，Z=4。超分子结构产生的原因是NH2基团形成了三个中心的S···H···F氢键和两个中心的N-H···F和N-H···S氢键。双（2-氨基-5-氟-3-甲基苯基）二硫醚的分子间和分子内氢键 J. E. Drake1, M. B. Hursthouse2, M. E. Light2, R. Maheshwari3, K.G. Ojha3, R. Ratnani3* 双（2-氨基-5-氟-3-甲基苯基）二硫醚通过分子间N-H···F和N-H···N
• Gupta, Rajni; Shrivastava, Vibha; Gupta, Archana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 413 - 416
  作者：Gupta, Rajni、Shrivastava, Vibha、Gupta, Archana、Verma、Gupta

  DOI：——

  日期：——
• Synthesis of 4H-1,4-Benzothiazine-1,1-dioxides (Sulfones) and Phenothiazine-5,5-dioxides (Sulfones)
  作者：Thandi Lal Kachhee、Vandana Gupta、D. C. Gautam、R. R. Gupta

  DOI：10.1080/104265090917790

  日期：2005.10

  The study of the oxidation behavior of 4H-1,4-benzothiazines and phenothiazines by 30% hydrogen peroxide in acetic acid results in the formation of 4H-1,4-benzothiazine-1,1-dioxides (sulfones) and 10H-phenothiazine-5,5-dioxides (sulfones) respectively. The purity of all the synthesized compounds has been checked by thin layer chromatography using silica "G" as an adsorbent in various nonaqueous solvent systems. Infra-red and proton-magnetic resonance spectral studies are also included.
• Synthesis of 7-ethoxy- and 7-fluoro-phenothiazines
  作者：Thandi Lal Kachhee、Vandana Gupta、D. C. Gautam、R. R. Gupta

  DOI：10.1080/714040982

  日期：2003.12.1

  Synthesis of 7-ethoxy- and 7-fluoro-phenothiazines is reported by Smiles rearrangement of 5-ethoxy- and 5-fluoro-2-formamido-2'nitrodiphenylsulfides. The later were obtained by the formylation of 2-amino-5-ethoxy/5-fluoro-2'-nitrodiphenylsulfides which were prepared by the condensation of 2-amino-5-ethoxyl-5-fluoro-benzenethiols with o-halonitrobenzenes.