methyl 5-(3-thienyl)-4-pentynoate | 1369558-72-4

• 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: methyl 5-(3-thienyl)-4-pentynoate
• 英文别名: Methyl 5-thiophen-3-ylpent-4-ynoate
• CAS: 1369558-72-4
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: UYCZPEMISIZTTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  methyl 5-(3-thienyl)-4-pentynoate 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-Thiophen-3-ylpent-4-ynoic acid
  参考文献：
  名称：

  Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes

  摘要：

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.

  DOI：

  10.1021/ja4032727
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 3-三甲硅基乙炔基噻吩 在 indium(III) chloride 、 三乙胺 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以89%的产率得到methyl 5-(3-thienyl)-4-pentynoate
  参考文献：
  名称：

  氯化铟（III）催化炔烷基硅烷与丙烯酸酯的共轭加成反应

  摘要：

  已经开发了在催化量的氯化铟（III）存在下通过将炔基硅烷共轭加成到丙烯酸酯上来合成δ，γ-炔基酯的新颖有效的方法。该方法提供了快速有效地获得取代的δ，γ-炔基酯的方法。

  DOI：

  10.1021/jo202628c

文献信息

• Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1<i>H</i>-fluorenes
  作者：Weidong Rao、Ming Joo Koh、Dan Li、Hajime Hirao、Philip Wai Hong Chan

  DOI：10.1021/ja4032727

  日期：2013.5.29

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.
• Indium(III) Chloride Catalyzed Conjugate Addition Reaction of Alkynylsilanes to Acrylate Esters
  作者：Yan-li Xu、Ying-ming Pan、Pei Liu、Heng-shan Wang、Xiao-yan Tian、Gui-fa Su

  DOI：10.1021/jo202628c

  日期：2012.4.6

  A novel and efficient procedure for the synthesis of δ,γ-alkynyl esters by the conjugate addition of alkynylsilanes to acrylate esters in the presence of a catalytic amount of indium(III) chloride has been developed. This method provides a rapid and efficient access to substituted δ,γ-alkynyl esters.

  已经开发了在催化量的氯化铟（III）存在下通过将炔基硅烷共轭加成到丙烯酸酯上来合成δ，γ-炔基酯的新颖有效的方法。该方法提供了快速有效地获得取代的δ，γ-炔基酯的方法。