3-Ethyl-oct-1-yne

• 分子结构分类: 有机化合物 - 碳化物
• 英文名称: 3-Ethyl-oct-1-yne
• 英文别名: 3-Ethyloct-1-yne
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: AJWPXTWKOCIRGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-Ethyl-oct-1-yne 、 2-异氰基-1,3-二异丙基苯 在 tris(bis(trimethylsilyl)amido)samarium(III) 、 1-氨基戊烷 作用下， 以 环己烷 为溶剂， 反应 9.0h， 生成 1-(2,6-diisopropylphenylimino)-4-ethylnon-2-yne 、 1-(2,6-diisopropylphenylimino)-4-ethylnon-2-yne
  参考文献：
  名称：

  Rare-Earth Silylamide-Catalyzed Monocoupling Reaction of Isocyanides with Terminal Alkynes

  摘要：

  Rare-earth silylamides, Ln[N(SiMe3)(2)](3) (Ln = Y, La, Sm, Yb), serve as good catalysts for monoinsertion of isocyanides into terminal alkynes in the presence of amine additives, leading to 1-aza-1,3-enyens in excellent yields. The reaction is applicable to a diverse set of terminal alkynes with various functionalities such as ethers, acetals, and amino groups. Larger metals (La and Sm) give a better performance than smaller ones (Y and Yb). Using less hindered primary amines and, in contrast, bulky isocyanides is crucial for the coupling reaction; otherwise, competitive oligomerization of the isocyanides occurs predominantly. In the mechanistic study, the rate-determining step of the reaction seems to be the first insertion of the isocyanides into rare-earth alkynides, which is followed by spontaneous protonation with the amine additives.

  DOI：

  10.1021/jo051193h