ethyl (3-methyl-2-thienyl)propiolate | 157889-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (3-methyl-2-thienyl)propiolate
• 英文别名: (3-methyl-[2]thienyl)-propiolic acid ethyl ester；(3-Methyl-[2]thienyl)-propiolsaeure-aethylester；Ethyl 3-(3-methylthiophen-2-yl)prop-2-ynoate
• CAS: 157889-59-3
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: DQQCRECIJRVQJB-UHFFFAOYSA-N

物化性质

• 沸点：
  291.0±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 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：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (3-methyl-2-thienyl)propiolate 在 sodium hydroxide 、 氯化亚砜 、 苄基三乙基氯化铵 作用下， 以 乙醚 、 水 为溶剂， 反应 126.0h， 生成 3-(3-methylthiophen-2-yl)prop-2-ynoyl chloride
  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：

  (α-ethoxycarbonyl-α-3-methyl-2-thenoylmethylene)triphenylphosphorane 500.0 ℃ 、133.32 Pa 条件下， 以88%的产率得到ethyl (3-methyl-2-thienyl)propiolate
  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

• Studies on the Chemistry of Heterocyclics. XXVII.¹ α,β-Acetylenic Acids and their Esters in the Thiophene Series
  作者：A. J. Osbahr、A. Vaitiekunas、F. F. Nord

  DOI：10.1021/ja01612a066

  日期：1955.4
• Aitken R. Alan, Seth Shirley, J. Chem. Soc. Perkin Trans., (1994) N 17, S 2461-2466
  作者：Aitken R. Alan, Seth Shirley

  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：——