1-methyl-5-undecynylamine | 112218-12-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-methyl-5-undecynylamine
• 英文别名: Dodec-6-YN-2-amine
• CAS: 112218-12-9
• 化学式: C₁₂H₂₃N
• 分子量: 181.321
• InChiKey: BIQFTUVCIJULIA-UHFFFAOYSA-N

物化性质

• 沸点：
  259.2±23.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-5-undecynylamine 在 sodium tetrachloroaurate(III) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以71%的产率得到6-hexyl-2-methyl-2,3,4,5-tetrahydropyridine
  参考文献：
  名称：

  Preparation of 2,3,4,5-Tetrahydropyridines from 5-Alkynylamines Under the Catalytic Action of Gold(III) Salts

  摘要：

  在金盐的催化作用下，5-烷基胺中的碳-碳三键发生分子内胺加成反应，生成2,3,4,5-四氢吡啶。多种蚁种的某些毒液成分就是通过应用这一反应来合成的。

  DOI：

  10.1055/s-1991-26621
• 作为产物：
  描述：

  十一碳-5-炔酸 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-methyl-5-undecynylamine
  参考文献：
  名称：

  Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines

  摘要：

  Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-pyrrolines in good yields; 5-alkynylamines afforded 2,3,4,5-tetrahydropyridines selectively. Treatment of 4-alkynylamines with Pd(II) afforded mixtures of both 5- and 6-membered cyclic imines. Applications to the synthesis of some naturally occurring alkaloids are also described.

  DOI：

  10.1021/jo00020a023

文献信息

• HETEROCYCLES, 25,(1987) NPEC. ISSUE, 297-300
  作者：

  DOI：——

  日期：——
• Fukuda, Yukitoshi; Utimoto, Kiitiro; Nozaki, Hitosi, Heterocycles, 1987, vol. 25, p. 297 - 300
  作者：Fukuda, Yukitoshi、Utimoto, Kiitiro、Nozaki, Hitosi

  DOI：——

  日期：——
• Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines
  作者：Yukitoshi Fukuda、Seijiro Matsubara、Kiitiro Utimoto

  DOI：10.1021/jo00020a023

  日期：1991.9

  Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-pyrrolines in good yields; 5-alkynylamines afforded 2,3,4,5-tetrahydropyridines selectively. Treatment of 4-alkynylamines with Pd(II) afforded mixtures of both 5- and 6-membered cyclic imines. Applications to the synthesis of some naturally occurring alkaloids are also described.
• Preparation of 2,3,4,5-Tetrahydropyridines from 5-Alkynylamines Under the Catalytic Action of Gold(III) Salts
  作者：Yukitoshi Fukuda、Kiitiro Utimoto

  DOI：10.1055/s-1991-26621

  日期：——

  Intramolecular addition of amine to carbon-carbon triple bonds in 5-alkynylamines produces 2,3,4,5-tetrahydropyridines under the catalytic action of an aurate salt. Some venom components of various ant species are synthesized by the application of this reaction.

  在金盐的催化作用下，5-烷基胺中的碳-碳三键发生分子内胺加成反应，生成2,3,4,5-四氢吡啶。多种蚁种的某些毒液成分就是通过应用这一反应来合成的。