2-p-chlorophenylthio-3-hydroxypropene | 97841-03-7

• 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-p-chlorophenylthio-3-hydroxypropene
• 英文别名: 2-(4-chlorophenyl)sulfanylprop-2-en-1-ol
• CAS: 97841-03-7
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: VPMOQDNQZUADCV-UHFFFAOYSA-N

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：
  0.11
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-p-chlorophenylthio-3-hydroxypropene 在 三羟甲基氨基甲烷 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 6.0h， 生成 [2-(4-Chloro-phenylsulfanyl)-allyl]-p-tolyl-(4-p-tolylsulfanyl-but-2-ynyl)-amine
  参考文献：
  名称：

  Mass spectral rearrangements ofN-(4′-arylthio-2′-butynyl)N-(2″-arylthio-2″-propenyl)-p-toluidines,N,N-bis(2′-arylthio-2′-propenyl)-p-toluidines and 1,2-bis(arylthio)acenaphthenes

  摘要：

  AbstractUnder electron impact the title compounds display, in addition to the sequential loss of the arylthio groups, the elimination of a bisaryl disulphide moiety, but they do not eliminate sulphur. The behaviour of the p‐toluidine derivatives supports the rearrangement pathway proposed earlier for N,N‐bis(4′‐arylthio‐2′‐butynyl)anilines.

  DOI：

  10.1002/oms.1210200312
• 作为产物：
  描述：

  2-丙炔-1-醇 、 4-氯苯硫酚 在 sodium 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以28%的产率得到2-p-chlorophenylthio-3-hydroxypropene
  参考文献：
  名称：

  Mass spectral rearrangements ofN-(4′-arylthio-2′-butynyl)N-(2″-arylthio-2″-propenyl)-p-toluidines,N,N-bis(2′-arylthio-2′-propenyl)-p-toluidines and 1,2-bis(arylthio)acenaphthenes

  摘要：

  AbstractUnder electron impact the title compounds display, in addition to the sequential loss of the arylthio groups, the elimination of a bisaryl disulphide moiety, but they do not eliminate sulphur. The behaviour of the p‐toluidine derivatives supports the rearrangement pathway proposed earlier for N,N‐bis(4′‐arylthio‐2′‐butynyl)anilines.

  DOI：

  10.1002/oms.1210200312

文献信息

• Synthesis of vinyl sulfides using glycerol as a recyclable solvent
  作者：Eder J. Lenardão、Márcio S. Silva、Renata G. Lara、Júnior M. Marczewski、Maraisa Sachini、Raquel G. Jacob、Diego Alves、Gelson Perin

  DOI：10.3998/ark.5550190.0012.222

  日期：——

  alkynes promoted by KF/Al2O3, using glycerol as recyclable solvent. This improved method furnishes selectively the corresponding anti-Markovnikov vinyl sulfides in good to excellent yields starting from terminal alkynes and aliphatic or aromatic thiols. The irradiation with microwaves facilitated the procedure and accelerates the reaction. The catalytic system and the glycerol can be re-used up to four

  描述了一种新的、清洁的、有效的协议，用于由 KF/Al2O3 促进的末端炔烃的氢硫醇化，使用甘油作为可回收溶剂。这种改进的方法从末端炔烃和脂肪族或芳香族硫醇开始，选择性地提供相应的反马尔科夫尼科夫乙烯基硫化物，产率良好至极好。微波辐射促进了该过程并加速了反应。催化系统和甘油可以重复使用多达四次，无需事先处理，并且具有相当的活性。
• Synthesis of vinyl sulfides via hydrothiolation of alkynes using Al2O3/KF under solvent-free conditions
  作者：Márcio S. Silva、Renata G. Lara、Júnior M. Marczewski、Raquel G. Jacob、Eder J. Lenardão、Gelson Perin

  DOI：10.1016/j.tetlet.2008.01.093

  日期：2008.3

  We present here a clean, solvent-free hydrothiolation of alkynes using solid supported catalyst (Al(2)O(3)/KF). This efficient and improved method selectively furnishes the corresponding anti-Markovnikov vinyl sulfides in good to excellent yields. The method is applicable for aliphatic and aromatic thiols and the catalytic system can be re-used up to two times without previous treatment and with comparable activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of vinyl sulfides under base-free conditions using selenium ionic liquid
  作者：Samuel Thurow、Naiana T. Ostosi、Samuel R. Mendes、Raquel G. Jacob、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2012.03.076

  日期：2012.5

  A very simple procedure is described for the efficient synthesis of vinyl sulfides by hydrothiolation of terminal alkynes using 1-n-butyl-3-methylimidazolium methylselenite, [bmim][SeO2(OCH3)]. The reaction proceeds cleanly under mild, base-free conditions and was performed with aromatic and aliphatic thiols. (C) 2012 Elsevier Ltd. All rights reserved.