ethyl 2-(methylsulfanyl)phenylpropiolate | 157889-58-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(methylsulfanyl)phenylpropiolate
• 英文别名: ethyl 3-(2-(methylthio)phenyl)propiolate；Ethyl 3-[2-(methylsulfanyl)phenyl]prop-2-ynoate；ethyl 3-(2-methylsulfanylphenyl)prop-2-ynoate
• CAS: 157889-58-2
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: DKFAIZQIIQTMKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(methylsulfanyl)phenylpropiolate 在 sodium hydroxide 、 氯化亚砜 、 苄基三乙基氯化铵 、 三乙胺 作用下， 以 乙醚 、 水 、 甲苯 为溶剂， 25.0~750.0 ℃ 、13.33 Pa 条件下， 反应 130.0h， 生成 2-ethynylbenzo[b]thiophene
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester

  摘要：

  Thirteen examples of stabilised alkynoyl ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 degrees C, to undergo extrusion of Ph(3)PO to give the diacetylenic esters 7 in moderate yield. At 750 degrees C the same ylides afforded terminal 1.3-diynes 8 although often in poor yield. For R = 2-MeSC(6)H(4) both 7 and 8 undergo secondary loss of Me(.) and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield. The first example of an alkadiynoyl ylide 11 has been prepared and is converted by FVP at 500 degrees C into the triacetylenic ester 12.

  DOI：

  10.1039/p19940002461
• 作为产物：
  描述：

  邻甲硫基苯甲酸酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 25.0~500.0 ℃ 、133.32 Pa 条件下， 反应 3.0h， 生成 ethyl 2-(methylsulfanyl)phenylpropiolate
  参考文献：
  名称：

  Aitken, R. Alan; Horsburg, Caroline E. R.; McCreadie, J. Graeme, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1727 - 1732

  摘要：

  DOI：

文献信息

• Pd/phenanthroline-catalyzed arylative cyclization of o-(1-alkynyl)thioanisoles: synthesis of 3-arylated benzo[b]thiophenes
  作者：Takayuki Yamauchi、Fumitoshi Shibahara、Toshiaki Murai

  DOI：10.1016/j.tetlet.2016.05.033

  日期：2016.7

  aryl iodides in the presence of catalytic amounts of [Pd(phen)2][PF6]2 resulted in the efficient formation of 3-arylated benzo[b]thiophenes, and a range of aryl iodides with electron-donating or -withdrawing groups could be used. While this reaction proceeded in the presence of aromatic and aliphatic groups on the terminal alkynyl carbon atom, silyl and alkoxycarbonyl groups hampered the reaction. Furthermore

  在催化量的[Pd（phen）2 ] [PF 6 ] 2存在下，邻-（1-炔基）硫代苯甲醚与芳基碘的芳基环化反应可有效形成3-芳基苯并[ b ]噻吩可以使用一定范围的带有给电子或吸电子基团的芳基碘化物。尽管该反应在末端炔基碳原子上存在芳族和脂族基团的情况下进行，但是甲硅烷基和烷氧基羰基基团阻碍了反应。此外，该方法可扩展到由N，N-二甲基-o合成3芳基吲哚-（1-炔基）苯胺。所有这些反应都通过裂解碳-杂原子键而顺利进行。除所需的环化产物外，在硫原子上使用邻-（羟丙基）苯基甲基取代基提供了异色满，其应通过羟基分子内攻击苄基碳原子而形成。
• AITKEN, R. ALAN;SETH, SHIRLEV, SYNLETT.,(1990) N, C. 212-213
  作者：AITKEN, R. ALAN、SETH, SHIRLEV

  DOI：——

  日期：——
• Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester
  作者：R. Alan Aitken、Shirley Seth

  DOI：10.1039/p19940002461

  日期：——

  Thirteen examples of stabilised alkynoyl ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 degrees C, to undergo extrusion of Ph(3)PO to give the diacetylenic esters 7 in moderate yield. At 750 degrees C the same ylides afforded terminal 1.3-diynes 8 although often in poor yield. For R = 2-MeSC(6)H(4) both 7 and 8 undergo secondary loss of Me(.) and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield. The first example of an alkadiynoyl ylide 11 has been prepared and is converted by FVP at 500 degrees C into the triacetylenic ester 12.
• Aitken, R. Alan; Horsburg, Caroline E. R.; McCreadie, J. Graeme, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1727 - 1732
  作者：Aitken, R. Alan、Horsburg, Caroline E. R.、McCreadie, J. Graeme、Seth, Shirley

  DOI：——

  日期：——