6,6′-disulfanediylbis(2-fluoroaniline) | 63755-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,6′-disulfanediylbis(2-fluoroaniline)
• 英文别名: 6,6'-dithiobis(2-fluoroaniline)；2-[(2-Amino-3-fluorophenyl)disulfanyl]-6-fluoroaniline
• CAS: 63755-09-9
• 化学式: C₁₂H₁₀F₂N₂S₂
• 分子量: 284.354
• InChiKey: NZMGNHOLSNFTJF-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: ethanol (64-17-5))
• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,6′-disulfanediylbis(2-fluoroaniline) 在 ammonium thioglycolate 、 对甲苯磺酸 作用下， 以 邻二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-fluoro-3,5-dihydro-2H-1,5-benzothiazepin-4-one
  参考文献：
  名称：

  A Simple and Efficient Method for Synthesis of Benzothiazepine Derivatives

  摘要：

  A series of 1,5-benzothiazepines were synthesized using disulfides and alpha,beta-unsaturated carbonyl or nitrite compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with alpha,beta-unsaturated carbonyl or nitrite compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2,2,4-trymethyl-3H-1,5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino-phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl)propionic acid ethyl esters (4) were produced. Subsequently, the 1,5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction.

  DOI：

  10.3987/com-10-12100
• 作为产物：
  描述：

  2-氨基-4-氟苯并噻唑 在 potassium hydroxide 作用下， 以 水 、 乙二醇 为溶剂， 生成 6,6′-disulfanediylbis(2-fluoroaniline)
  参考文献：
  名称：

  A Simple and Efficient Method for Synthesis of Benzothiazepine Derivatives

  摘要：

  A series of 1,5-benzothiazepines were synthesized using disulfides and alpha,beta-unsaturated carbonyl or nitrite compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with alpha,beta-unsaturated carbonyl or nitrite compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2,2,4-trymethyl-3H-1,5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino-phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl)propionic acid ethyl esters (4) were produced. Subsequently, the 1,5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction.

  DOI：

  10.3987/com-10-12100

文献信息

• Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: metal sulfide–disulfide dynamic interchange reaction
  作者：Chunqing Lou、Ning Zhu、Ronghua Fan、Hailong Hong、Limin Han、Jianbin Zhang、Quanling Suo

  DOI：10.1039/c6gc03053j

  日期：——

  A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by metal sulfide in water is described. This synthetic methodology could be used to prepare...

  描述了一种方便有效的方法，该方法由金属硫化物在水中从二硫化物和CS2合成2-巯基苯并噻唑。这种综合方法可用于制备...
• 一种绿色合成2-巯基苯并噻唑类衍生物的方 法
  申请人：内蒙古工业大学

  公开号：CN105949147B

  公开（公告）日：2018-10-19

  本发明提供一种绿色合成2‑巯基苯并噻唑类衍生物的方法，该方法包括：使邻胺基芳香二硫化物、CS2、金属硫化物和溶剂接触，得到2‑巯基苯并噻唑类衍生物，所述溶剂为水、低碳醇、DMSO、DMF、NMP和1,4‑二氧六环中的至少一种。同现有技术相比，本发明利用邻氨基芳香二硫化物与二硫化碳发生反应，快速高效地合成了2‑巯基苯并噻唑类衍生物，所用原料稳定易得、成本低廉，合成方法操作简便、步骤短、产率高、产品易于纯化。
• Catalyst-free reductive cyclization of bis(2-aminophenyl) disulfide with CO₂ in the presence of BH₃NH₃ to synthesize 2-unsubstituted benzothiazole derivatives
  作者：Xiao Li、Zhenbao Liu、Hailong Hong、Limin Han、Ning Zhu

  DOI：10.1039/d2ra03134e

  日期：——

  cyclization of various disulfides using BH3NH3 as a reductant and CO2 as a C1 resource was developed. The desired 2-unsubstituted benzothiazole derivatives were obtained in good to excellent yields. Moreover, mechanism investigation demonstrated that BH3NH3 played an important role in the formation of benzothiazole. As a reducing agent, BH3NH3 reduced CO2 and cleaved the S–S bond of the disulfide efficiently

  开发了一种使用 BH 3 NH 3作为还原剂和 CO 2作为 C1 资源的各种二硫化物还原环化的高效且无催化剂的方法。以良好至优异的产率获得所需的 2-未取代的苯并噻唑衍生物。此外，机理研究表明，BH 3 NH 3在苯并噻唑的形成中起重要作用。作为还原剂，BH 3 NH 3还原CO 2并有效地裂解二硫键的S-S键。此外，氨基的N-H键也被BH 3 NH 3活化。. 据我们所知，这是一种前所未有的无催化剂方案，用于从双（2-氨基苯基）二硫化物和 CO 2合成 2-未取代的苯并噻唑。
• MAZZONE G.; PAPPALARDO G., FARMACO. ED. SCI., 1977, 32, NO 5,
  作者：MAZZONE G.、 PAPPALARDO G.

  DOI：——

  日期：——
• CN115611789
  申请人：——

  公开号：——

  公开（公告）日：——