α-[(2-pyrimidyl)thio]acetonitrile | 74537-75-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: α-[(2-pyrimidyl)thio]acetonitrile
• 英文别名: (2-Pyrimidylthio)acetonitrile；pyrimidin-2-ylsulfanyl-acetonitrile；2--acetonitril；2-(2-Pyrimidinylsulfanyl)acetonitrile；2-pyrimidin-2-ylsulfanylacetonitrile
• CAS: 74537-75-0
• 化学式: C₆H₅N₃S
• mdl: MFCD02325563
• 分子量: 151.192
• InChiKey: VDADVILLLUBBNV-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: methanol (67-56-1))
• 沸点：
  300.1±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-[(2-pyrimidyl)thio]acetonitrile 在 C₂F₆NO₄S₂^(1-)*C₁₃H₁₆IN₂O⁽¹⁺⁾ 、 triethylamine tris(hydrogen fluoride) 作用下， 以72%的产率得到α-fluoro-α-[(2-pyrimidyl)thio]acetonitrile
  参考文献：
  名称：

  使用特定任务的离子液体进行选择性电催化氟化

  摘要：

  通过使用任务特定的碘芳烃离子液体作为离子液体氟化氢盐的介体，首次成功地进行了有机化合物的高选择性间接阳极氟化。

  DOI：

  10.1021/ol9028836
• 作为产物：
  描述：

  氯乙腈 、 2-巯基嘧啶 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到α-[(2-pyrimidyl)thio]acetonitrile
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides

  摘要：

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.

  DOI：

  10.1021/jo9909857

文献信息

• Pyrimidinylthioacrylic acid derivatives useful as herbicides
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0571856A1

  公开（公告）日：1993-12-01

  The present invention relates to novel pyrimidinylthioacrylic acid derivatives of the formula (I) wherein R¹represents hydrogen or in each case optionally substituted C₁₋₆ alkyl, C₂₋₄ alkenyl or C₂₋₄ alkynyl, R²represents hydrogen or optionally substituted C₁₋₆ alkyl, or alkali salts, R³ and R⁴each independently represent C₁₋₄ alkyl, C₁₋₄ alkoxy, halogeno-C₁₋₄ alkyl, halogeno-C₁₋₄ alkoxy or halogen, and R⁵represents hydrogen, or in each case optionally substituted C₁₋₆ alkyl, phenyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, or a heterocyclic ring, or an alkali metal salt, alkali earth metal or organic ammonium salt of pyrimidinylthioacrylic acid derivatives of the formula (I), to processes for their preparation and their use as herbicides, as well as to novel intermediates and to a process for their preparation.

  本发明涉及公式（I）的新型嘧啶基硫丙酸衍生物，其中R¹代表氢或每种情况下可选择取代的C₁₋₆烷基、C₂₋₄烯基或C₂₋₄炔基，R²代表氢或可选择取代的C₁₋₆烷基，或者碱盐，R³和R⁴各自独立地代表C₁₋₄烷基、C₁₋₄烷氧基、卤代C₁₋₄烷基、卤代C₁₋₄烷氧基或卤素，R⁵代表氢，或每种情况下可选择取代的C₁₋₆烷基、苯基、C₂₋₄烯基、C₂₋₄炔基或杂环，或者公式（I）的嘧啶基硫丙酸衍生物的碱金属盐、碱土金属或有机铵盐，以及它们的制备方法和作为除草剂的用途，以及新型中间体和其制备方法。
• Synthesis of medium cyclic and macrocyclic compounds. Part 5. An efficient construction of germacrane skeleton via the substituted (phenylthio)acetonitriles. The synthesis of (-)-dihydrogermacrene D
  作者：Takeshi Kitahara、Kenji Mori

  DOI：10.1021/jo00192a007

  日期：1984.9
• Electrolytic Partial Fluorination of Organic Compounds. 35.¹ Anodic Fluorination of 2-Pyrimidyl, 2-Pyridyl, and 2-Quinazolinonyl Sulfides
  作者：Kamal M. Dawood、Seiichiro Higashiya、Yankun Hou、Toshio Fuchigami

  DOI：10.1021/jo9909857

  日期：1999.10.1

  Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron(EWG) withdrawing group at the position alpha to the sulfur atom was successfully carried out using Et4NF . nHF (n = 3, 4) or Et3N . 3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with alpha,alpha-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly alpha-fluorination along with unexpected ipso-fluorination through anodic desulfurization.
• Use of Task-Specific Ionic Liquid for Selective Electrocatalytic Fluorination
  作者：Takahiro Sawamura、Shunsuke Kuribayashi、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1021/ol9028836

  日期：2010.2.5

  Highly selective indirect anodic fluorination of organic compounds was successfully carried out for the first time by using a task-specific ionic liquid of iodoarene as a mediator in ionic liquid hydrogen fluoride salts.

  通过使用任务特定的碘芳烃离子液体作为离子液体氟化氢盐的介体，首次成功地进行了有机化合物的高选择性间接阳极氟化。