2-methyl-3-(phenylthio)propionitrile | 118449-60-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-3-(phenylthio)propionitrile
• 英文别名: β-phenylsulfanyl-isobutyronitrile；β-Phenylmercapto-isobutyronitril；2-Methyl-3-(phenylthio)propanenitrile；2-methyl-3-phenylsulfanylpropanenitrile
• CAS: 118449-60-8
• 化学式: C₁₀H₁₁NS
• mdl: MFCD00019811
• 分子量: 177.27
• InChiKey: UTJFJARVAOHQLA-UHFFFAOYSA-N

物化性质

• 熔点：
  79-79.6 °C
• 沸点：
  79 °C(Press: 0.04 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(phenylthio)propionitrile 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以80%的产率得到3-Benzenesulfinyl-2-methyl-propionitrile
  参考文献：
  名称：

  Synthesis of β-fluoro-α,β-unsaturated esters and nitriles via a fluoro-pummerer rearrangement

  摘要：

  DOI：

  10.1016/s0040-4039(00)97909-7
• 作为产物：
  描述：

  3-Benzenesulfinyl-2-methyl-propionitrile 生成 2-methyl-3-(phenylthio)propionitrile
  参考文献：
  名称：

  KRISHNAN, GANAPATHY;SAMPSON, PAUL, TETRAHEDRON LETT., 31,(1990) N9, C. 5609-5612

  摘要：

  DOI：

文献信息

• A Simple, Efficient, and Green Procedure for the 1,4-Addition of Thiols to Conjugated Alkenes and Alkynes Catalyzed by Sodium Acetate in Aqueous Medium
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1071/ch06455

  日期：——

  A benign and inexpensive salt, sodium acetate, efficiently catalyzes 1,4-addition of thiols to a variety of conjugated alkenes such as α,β-unsaturated ketones, aldehydes, carboxylic esters, nitriles, nitro compounds, and chalcones in aqueous THF. The reactions are clean, fast, and high yielding.

  一种温和且廉价的盐乙酸钠可在 THF 水溶液中有效催化硫醇与各种共轭烯烃（例如 α,β-不饱和酮、醛、羧酸酯、腈、硝基化合物和查耳酮）的 1,4-加成反应。反应干净、快速且产率高。
• Indium(I) Iodide-Promoted Cleavage of Dialkyl Disulfides and Subsequent Michael Addition of Thiolate Anions to Conjugated Carbonyl Compounds
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1055/s-2004-825583

  日期：——

  Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions which then undergo facile addition to α, β -unsaturated ketones, aldehydes, carboxylic esters and nitriles under neutral conditions producing corresponding β-keto or β-cyano sulfides in high yields. There are several examples of dialkyl/diaryl disulfides and activated alkenes participating in this reaction.

  碘化铟 (I) 促进二烷基二硫化物的裂解，生成硫醇阴离子，然后在中性条件下轻松加成到 α、β-不饱和酮、醛、羧酸酯和腈，以高产率生成相应的 β-酮或 β-氰基硫化物。有几个二烷基/二芳基二硫化物和活化烯烃参与该反应的例子。
• KF/Al₂O₃-Mediated Michael Addition of Thiols to Electron‐Deficient Olefins
  作者：F. Matloubi Moghaddam、G. Rezanejade Bardajee、R. Oftadeh Chadorneshine Veranlou

  DOI：10.1080/00397910500189783

  日期：2005.9.1

  Abstract Potassium fluoride supported on alumina efficiently catalyzes Michael addition of aromatic and aliphatic thiols to a variety of conjugated alkenes such as α,β‐unsaturated carbonyl compounds, carboxylic esters, amides, nitriles and chalcones. The Michael adducts are produced in good to excellent yields and relatively in short times. The catalyst can be recycled for subsequent reactions without

  摘要 氧化铝负载的氟化钾有效地催化芳香族和脂肪族硫醇与各种共轭烯烃的迈克尔加成反应，如α,β-不饱和羰基化合物、羧酸酯、酰胺、腈和查耳酮。迈克尔加合物以良好到极好的收率和相对较短的时间产生。催化剂可以循环用于后续反应，而不会显着降低效率。
• Efficient Synthesis of β‐Alkyl/Arylsulfanyl Carbonyl Compounds by In‐TMSCl‐Promoted Cleavage of Dialkyl/Diaryl Disulfides and Subsequent Michael Addition
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1080/00397910701229859

  日期：2007.5

  Abstract A convenient and efficient procedure for the synthesis of β‐alkyl/arylsulfanyl carbonyl compounds has been developed by a simple one‐pot reaction of dialkyl/diaryl sulfides with α,β‐unsaturated aldehydes, ketones, carboxylic esters, and nitriles in presence of indium and trimethylsilyl chloride under sonication.

  摘要 通过二烷基/二芳基硫化物与 α,β-不饱和醛、酮、羧酸酯和腈在超声处理下的铟和三甲基氯硅烷。
• Indium(I) iodide promoted cleavage of dialkyl disulfides — Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
  作者：Brindaban C Ranu、Tanmay Mandal

  DOI：10.1139/v06-065

  日期：2006.5.1

  promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing

  碘化铟 (I) 促进二烷基二硫化物的裂解，生成硫醇阴离子，然后在中性条件下轻松加成到 α,β-不饱和酮、醛、羧酸酯和腈，产生相应的 β-酮硫化物或 β-氰基硫化物。该策略也已用于在氯化铟 (III) 存在下通过硫醇阴离子对环氧化物进行区域选择性亲核开环，产生相应的 β-羟基苯基硫化物。反应通常非常干净、产率高且相当快。因此，利用这种裂解反应开发了合成 β-酮硫化物或 β-氰基硫化物和 β-羟烷基硫化物的简便方法。环氧化物，β-羟基硫化物。