(E)-(4-氰基苯基)偶氮苯基硫化物 | 132555-11-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 中文名称: (E)-(4-氰基苯基)偶氮苯基硫化物
• 英文名称: (E)-(4-Cyanophenyl)azo phenyl sulfide
• CAS: 132555-11-4
• 化学式: C₁₃H₉N₃S
• 分子量: 239.301
• InChiKey: VNBPLDGINSKTMU-FOCLMDBBSA-N

物化性质

• 沸点：
  411.0±47.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-(4-氰基苯基)偶氮苯基硫化物 、 tetrabutylammonium phenolate 以14%的产率得到
  参考文献：
  名称：

  PETRILLO, GIOVANNI;NOVI, MARINO;CARLO, DELLERBA, TETRAHEDRON LETT., 30,(1989) N9, C. 6911-6912

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium thiophenolate 、 alkaline earth salt of/the/ methylsulfuric acid 反应 0.08h， 以82%的产率得到(E)-(4-氰基苯基)偶氮苯基硫化物
  参考文献：
  名称：

  Fast, efficient and convenient method for the preparation of arylazo sulfides using aryl diazonium silica sulfates under mild and solvent-free conditions

  摘要：

  An efficient, fast, and straightforward procedure for the synthesis of arylazo sulfides and arylazo thiosulfonates is described in the present paper by using aryl diazonium silica sulfates and sodium thiolates. Using the present method, different kinds of aryl diazonium silica sulfates, containing electron-withdrawing groups as well as electron-donating groups, were rapidly converted to the corresponding arylazo sulfides in good yield and short reaction time. These reactions were carried out at room temperature under mild and solvent-free conditions. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields are the advantages of this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.02.010

文献信息

• SRN1C-arylation of potassium aryloxides by arylazo phenyl or tert- butyl sulfides in DMSO
  作者：Giovanni Petrillo、Marino Novi、Carlo Dell Erba、Cinzia Tavani、Giovanni Berta

  DOI：10.1016/s0040-4020(01)90095-x

  日期：1990.1

  Aryloxide ions (Ar'O-) behave as C-nucleophiles towards diazosulfides (ArN=NSR; R = Ph, But) leading to unsymmetrical hydroxybiaryls (ArAr'OH) via C-C coupling. The reaction is particularly suited for the synthesis of terms which contain electron-withdrawing groups on the Ar moiety. The SRN1 mechanism is proposed on the grounds of experimental evidences.

  芳氧基离子（Ar'O - ）表现为向diazosulfides C-亲核试剂（ARN = NSR; R = PH，卜吨），导致不对称hydroxybiaryls（ArAr'OH）通过CC耦合。该反应特别适合于在Ar部分上包含吸电子基团的项的合成。S RN 1机制是根据实验证据提出的。
• Arylation of potassium 2,4-pentanedionate via SRN1 on diazosulfides
  作者：Carlo Dell'Erba、Marino Novi、Giovanni Petrillo、Cinzia Tavani、Paolo Bellandi

  DOI：10.1016/s0040-4020(01)80929-7

  日期：1991.1

  Potassium 2,4-pentanedionate reacts with diazosulfides (E)-1 and (Z)-2 in DMSO to give 3-aryl-2,4-pentanediones 3 via an S(RN)1 process. Advantages and drawbacks of such new access to 3 are reported together with relevant mechanistic implications.
• Very fast, in-cage, recombination of a radical with a nucleophile. Arylazo sulfides in SRN1 aromatic nucleophilic substitutions
  作者：Carlo Dell'Erba、Abdelaziz Houmam、Marino Novi、Giovanni Petrillo、Jean Pinson

  DOI：10.1021/jo00062a007

  日期：1993.5

  The cyclic voltammograms of (E)-(4-cyanophenyl)azo (1a) and (E)-(4-nitrophenyl)azo phenyl sulfide (1b) as well as of (E)- and (Z)-(4-cyanophenyl)azo tert-butyl sulfide [(E)-1c and (Z)-1c] evidence an extremely effective recombination between the aryl radical and the thiolate anion originating from the decomposition of the radical anions of the azo sulfides. Solvent changes and the addition of CN- as an ''external' nucleophile point to a cage effect as the cause of such efficient S(RN)1 reactions leading to the corresponding aryl phenyl or aryl tert-butyl sulfides 2a-c. In the case of (4-cyanophenyl)-azo tert-butyl sulfide [(E)-1c and (Z)-1c], trapping by the ''external'' nucleophile is more efficient with the (E)-isomer than with the (Z)-isomer, and the possible causes of this effect are discussed.
• PETRILLO, GIOVANNI;NOVI, MARINO;GARBARINO, GIACOMO;DELLERBA, CARLO, TETRAHEDRON, 43,(1987) N 20, 4625-4634
  作者：PETRILLO, GIOVANNI、NOVI, MARINO、GARBARINO, GIACOMO、DELLERBA, CARLO

  DOI：——

  日期：——
• NOVI M.; PETRILLO G.; DELLERBA C., TETRAHEDRON LETT., 28,(1987) N 12, 1345-1348
  作者：NOVI M.、 PETRILLO G.、 DELLERBA C.

  DOI：——

  日期：——