(E)-(4-Cyanophenyl)azo-tert-butyl-sulfide | 29577-89-7

• 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: (E)-(4-Cyanophenyl)azo-tert-butyl-sulfide
• 英文别名: (E)-(4-cyanophenyl)azo tert-butyl sulfide；(E)-4-Cyanophenylazo tert-butylsulfide
• CAS: 29577-89-7
• 化学式: C₁₁H₁₃N₃S
• 分子量: 219.31
• InChiKey: HRKQABHGIYJLOK-BUHFOSPRSA-N

物化性质

• 熔点：
  103.6-104.7 °C(Solv: methanol (67-56-1))
• 沸点：
  343.8±44.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-Cyanophenyl)azo-tert-butyl-sulfide 、 potassium acetylacetonate 以 二甲基亚砜 为溶剂， 以73%的产率得到3-(4-Cyanophenyl)-2,4-pentanedione
  参考文献：
  名称：

  Arylation of potassium 2,4-pentanedionate via SRN1 on diazosulfides

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)80929-7
• 作为产物：
  描述：

  (Z)-(4-氰基苯基)偶氮叔丁基硫醚 以 四氯化碳 为溶剂， 生成 (E)-(4-Cyanophenyl)azo-tert-butyl-sulfide
  参考文献：
  名称：

  Arylation of potassium 2,4-pentanedionate via SRN1 on diazosulfides

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)80929-7

文献信息

• 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.
• DELL, ERBA CARLO;NOVI, MARINO;PETRILLO, GIOVANNI;TOVARNI, CINZIA;BELANDI,+, TETRAHEDRON, 47,(1991) N, C. 333-342
  作者：DELL, ERBA CARLO、NOVI, MARINO、PETRILLO, GIOVANNI、TOVARNI, CINZIA、BELANDI,+

  DOI：——

  日期：——