2-甲基-2-(苯基硫代)丙二腈 | 150194-63-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-甲基-2-(苯基硫代)丙二腈
• 英文名称: 2-Methyl-2-(phenylthio)malononitrile
• 英文别名: 2-Methyl-2-phenylsulfanylpropanedinitrile；2-methyl-2-phenylsulfanylpropanedinitrile
• CAS: 150194-63-1
• 化学式: C₁₀H₈N₂S
• 分子量: 188.253
• InChiKey: WSLITGMCEGZBPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  299.3±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-oxononoxy)-2-(1H)-pyridinethione 、 2-甲基-2-(苯基硫代)丙二腈 以 苯 为溶剂， 反应 20.0h， 生成 2-(octylthio)pyridine 、 n-octylsulfanylbenzene 、
  参考文献：
  名称：

  Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals

  摘要：

  Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio) phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.

  DOI：

  10.1021/jo00069a036
• 作为产物：
  描述：

  1-异喹啉硼酸 、 苯次磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以83%的产率得到2-甲基-2-(苯基硫代)丙二腈
  参考文献：
  名称：

  Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals

  摘要：

  Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio) phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.

  DOI：

  10.1021/jo00069a036

文献信息

• Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals
  作者：Dennis P. Curran、Amanda A. Martin-Esker、Sung Bo Ko、Martin Newcomb

  DOI：10.1021/jo00069a036

  日期：1993.8

  Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio) phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.