1-methylsulfanyl-1-methylsulfinylprop-1-ene | 777892-10-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 1-methylsulfanyl-1-methylsulfinylprop-1-ene
• 英文别名: (Z)-1-methanesulfinyl-1-methylsulfanyl-propene；methylketene dimethyl dithioacetal (Z)-S-oxide；(Z)-1-methylsulfanyl-1-methylsulfinylprop-1-ene
• CAS: 777892-10-1
• 化学式: C₅H₁₀OS₂
• 分子量: 150.266
• InChiKey: GMYAITXHIJIVSU-PLNGDYQASA-N

物化性质

• 沸点：
  319.5±34.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-O-Acetyl-propyl-thioacetal 在 氢氧化钾 、 sodium periodate 作用下， 以 甲醇 、 苯 为溶剂， 生成 1-methylsulfanyl-1-methylsulfinylprop-1-ene
  参考文献：
  名称：

  乙炔硫缩醛一氧化碳：新颖且通用的一类二碳迈克尔受体

  摘要：

  DOI：

  10.1016/s0040-4039(01)87317-2

文献信息

• Two-Step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling
  作者：Kei Murakami、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1246/bcsj.20140241

  日期：2014.12.15

  Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family.

  已成功实现从简单酚类化合物合成多取代苯并呋喃的实用且多样化的合成方法，采用了Pummerer环化/交叉偶联序列。酚类与酮硫酰单氧化物（KDMs）在三氟乙酸酐的帮助下发生操作简便、迅速的反应，生成相应的2-甲基硫苯并[b]呋喃。该反应的适用范围涵盖了具有广泛取代基的酚类和KDMs。环化产物中的剩余甲基硫基团通过我们特别改进的交叉偶联反应转化为各种芳基。此两步法合成多取代苯并呋喃的能力足以合成高度荧光的苯并呋喃衍生物，以及天然存在的Eupomatenoid家族。
• Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides
  作者：Kei Murakami、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1246/bcsj.20130148

  日期：2013.10.15

  Practical syntheses of substituted ketene dithioacetal monoxides (KDMs) from the corresponding aldehydes or ethyl trifluoroacetate are described. Newly developed procedures are scalable and versatile to provide aryl-, alkyl-, and trifluoromethyl-substituted KDMs in gram scales.

  从相应的醛或三氟乙酸乙酯合成取代的酮硫代乙酰单氧化物（KDMs）的实用合成方法被描述。新开发的程序具有可扩展性和多样性，能够以克级规模提供芳基、烷基和三氟甲基取代的KDMs。
• Highly Chemoselective Oxidation of Dithioester Enethiolates to Sulfenates:  Application to the Synthesis of Ketene Dithioacetal <i>S</i>-Oxides
  作者：Franck Sandrinelli、Gaëlle Fontaine、Stéphane Perrio、Pierre Beslin

  DOI：10.1021/jo0492362

  日期：2004.10.1

  Enethiolates derived from dithioesters were efficiently converted into the corresponding vinyl sulfenates by oxidation with a unique N-sulfonyloxaziridine la derived from pinacolone. Subsequent alkylation with alkyl halides led to ketene dithioacetal S-oxides in good to excellent yields.