4-methylphenyl prop-1-enyl sulfide | 39815-00-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-methylphenyl prop-1-enyl sulfide
• 英文别名: prop-1-en-1-yl(p-tolyl)sulfane；1-p-Tolyl-mercapto-2-methyl-ethylen；2-p-Toluolmercapto-1-methylethylen；Propenyl-(1)-p-tolyl-sulfid；1-Methyl-4-[(prop-1-en-1-yl)sulfanyl]benzene；1-methyl-4-prop-1-enylsulfanylbenzene
• CAS: 39815-00-4
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: QBBWCKDSFNEULN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methylphenyl prop-1-enyl sulfide 生成 (Z)-Propenyl-p-tolyl-vinyl-sulfoxid
  参考文献：
  名称：

  Annunziata,R.; Cinquini,M., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1684 - 1686

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl (p-tolyl)sulfide 生成 4-methylphenyl prop-1-enyl sulfide
  参考文献：
  名称：

  Karaulowa; Meilanowa; Galpern, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3034

  摘要：

  DOI：

文献信息

• Flash vacuum pyrolysis of alkoxycarbonyl/sulfinyl stabilised phosphorus ylides: generation and intramolecular insertion of alkoxycarbonyl(sulfenyl)carbenes
  作者：R. Alan Aitken、Martin J. Drysdale、Bruce M. Ryan

  DOI：10.1039/c39940000805

  日期：——

  Flash vacuum pyrolysis of phosphorus ylides stabilised both by ester and sulfinyl groups results mainly in extrusion of Ph3PO to generate alkoxycarbonyl(sulfenyl)carbenes; these undergo intramolecular insertion into CH of the alkoxycarbonyl group giving β-lactones which under the conditions lose CO2 to afford alkenyl sulfides.

  酯和亚磺酰基均稳定的磷化磷的闪蒸真空热解主要导致Ph 3 PO挤出生成烷氧基羰基（亚磺酰基）卡宾；这些经过烷氧基羰基分子内插入CH中，得到β-内酯，该β-内酯在失去CO 2的条件下得到链烯基硫化物。
• Syntheses of 2-Azetidinone (β-Lactam) Ring by Chlorosulfonyl Isocyanate (CSI)
  作者：KOICHI HIRAI、HIDEBUMI MATSUDA、YUKICHI KISHIDA

  DOI：10.1248/cpb.21.1090

  日期：——

  Attempts were made to prepare sulfur substituted 2-azetidinones by the reaction of vinylsulfide with chlorosulfonyl isocyanate (CSI). The main product of the reaction of β-methylthiostyrene (I) with CSI was pyridone derivative (II), but in the case of 1-phenylthio-1-propene (V) the main products were dihydrouracil derivatives (VI and VII) and acrylic acid derivatives (VIII and IX). Reaction of 1-p-chloro- or p-methylphenylthio-1-propene (Xa and b) with CSI in dry ether at -30°gave the desired 2-azetidinone (β-lactam) derivatives (XIa and b) in 63 and 66.4% isolated yield respectively.

  尝试通过乙烯硫化物与氯磺酰异氰酸酯（CSI）反应制备硫代2-氮杂丁烷酮。β-甲硫基苯乙烯（I）与CSI反应的主要产物是吡啶酮衍生物（II），但在1-苯硫基-1-丙烯（V）的情况下，主要产物是二氢尿嘧啶衍生物（VI 和 VII）以及丙烯酸衍生物（VIII 和 IX）。1-p-氯或p-甲苯硫基-1-丙烯（Xa 和 b）与CSI在干燥的乙醚中于-30°C反应，得到所需的2-氮杂丁烷酮（β-内酰胺）衍生物（XIa 和 b），其分离收率分别为63% 和 66.4%。
• Aitken, R. Alan; Armstrong, Jill M.; Drysdale, Martin J., Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 593 - 604
  作者：Aitken, R. Alan、Armstrong, Jill M.、Drysdale, Martin J.、Ross, Fiona C.、Ryan, Bruce M.

  DOI：——

  日期：——
• Ghersetti,S. et al., Gazzetta Chimica Italiana, 1961, vol. 91, p. 620 - 632
  作者：Ghersetti,S. et al.

  DOI：——

  日期：——
• Insertion of Carbon Monoxide into Allylic Carbon-Sulfur Bonds Catalyzed by Palladium and Ruthenium Complexes
  作者：Cathleen M. Crudden、Howard Alper

  DOI：10.1021/jo00122a045

  日期：1995.9

  The metal complex-catalyzed insertion of carbon monoxide into the C-S bond of various allylic sulfides affords thioesters in up to 88% yield. The reaction is catalyzed by various palladium complexes, with concomitant isomerization of the olefin into conjugation with the carbonyl group. In these cases, only the trans isomer was detected by H-1 NMR spectroscopy. Ruthenium complexes also catalyzed the carbonylation but the initially formed beta,gamma-thioester was not isomerized.