ethyl 5-(2-methoxyphenyl)penta-2,4-diynoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-(2-methoxyphenyl)penta-2,4-diynoate
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: VHGOIYLYYVLGDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-methoxyphenyl)penta-2,4-diynoate 、 氯化亚砜 、 sodium hydroxide 生成 5-(2-methoxyphenyl)penta-2,4-diynoyl chloride
  参考文献：
  名称：

  AITKEN, R. ALAN;SETH, SHIRLEV, SYNLETT.,(1990) N, C. 212-213

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基3-(2-甲氧基苯基)-2-丙炔酸酯 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， 25.0~500.0 ℃ 、13.33 Pa 条件下， 反应 130.0h， 生成 ethyl 5-(2-methoxyphenyl)penta-2,4-diynoate
  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

文献信息

• One‐pot synthesis of unsymmetrical 1,3‐butadiyne derivatives
  作者：Zhicai Zhao

  DOI：10.1002/bkcs.12762

  日期：2023.10

  An efficient co-operative Ni/Cu system for Cadiot–Chodkiewicz coupling utilizes CaC2 as the alkyne source. The advantage of this cross-coupling reaction lies in the low cost of using cheap and readily available raw materials and the simplicity of operation. A series of functionalized diaryl, aryl-alkyl, and aryl-heteroaryl 1,3-diynes are obtained in moderate to high yields.

  Cadiot-Chodkiewicz 耦合的高效协同 Ni/Cu 系统利用 CaC 2作为炔烃源。这种交叉偶联反应的优点在于使用廉价易得的原材料成本低且操作简单。以中等到高产率获得了一系列官能化二芳基、芳基-烷基和芳基-杂芳基1,3-二炔。
• AITKEN, R. ALAN;SETH, SHIRLEV, SYNLETT.,(1990) N, C. 212-213
  作者：AITKEN, R. ALAN、SETH, SHIRLEV

  DOI：——

  日期：——
• 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.