N-Methyl-3-hexyn-1-amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Methyl-3-hexyn-1-amine
• 英文别名: N-methylhex-3-yn-1-amine
• 化学式: C₇H₁₃N
• mdl: MFCD19220283
• 分子量: 111.187
• InChiKey: AIMCKQUTXNDRGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Methyl-3-hexyn-1-amine 460.0 ℃ 、6.67 kPa 条件下， 以100%的产率得到1-methyl-2-ethylidenepyrrolidine
  参考文献：
  名称：

  β-氨基烯烃和β-氨基乙炔的热解反应可形成逆烯反应和2-亚烷基亚吡咯烷

  摘要：

  具有末端炔键的β-氨基乙炔和β-氨基烯烃的热解反应可发生逆烯反应，其中氮充当氢供体，而炔键末端上的烷基取代导致新的，容易的环化成α 2-亚烷基亚吡咯烷。

  DOI：

  10.1039/c39840001429
• 作为产物：
  描述：

  3-已炔-1-醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 作用下， 反应 96.0h， 生成 N-Methyl-3-hexyn-1-amine
  参考文献：
  名称：

  Acetylenes as potential antarafacial components in concerted reactions. Formation of pyrroles from thermolyses of propargyl amines, of a dihydrofuran from a propargylic ether, and of an ethylidenepyrrolidine from a .beta.-amino acetylene

  摘要：

  A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in [2 + 2] processes. The cyclization competes with the normally favored acetylenic retro-ene reaction. Propargylic amines, without substituents whose presence would hinder a tight cyclic transition state, yield intermediate pyrrolines whose subsequent hydrogen elimination affords pyrroles in small amounts. The same process in 2-ethynyltetrahydropyran affords 8-oxabicyclo[3.2.1]octane in 35% yield. A related thermal reaction of N-methyl-3-hexyn-1-amine provides a quantitative transformation to N-methyl-2-ethylidenepyrrolidine in a nominal [2s + 2a + 2s + 2s] Mobius process, wherein the acetylenic unit is the antarafacial component. Evidence for concertedness in these reactions is discussed.

  DOI：

  10.1021/jo00071a015

文献信息

• Retro-ene reactions and 2-alkylidenepyrrolidine formation from thermolyses of β-amino-olefins and β-aminoacetylenes
  作者：Alfred Viola、John S. Locke

  DOI：10.1039/c39840001429

  日期：——

  Thermolyses of β-aminoacetylenes with a terminal acetylenic bond and of β-amino-olefins afford retro-ene reactions in which nitrogen acts as the hydrogen donor, whereas alkyl subsitution on the terminus of the acetylenic bond leads to a novel, facile cyclization to a 2-alkylidenepyrrolidine.

  具有末端炔键的β-氨基乙炔和β-氨基烯烃的热解反应可发生逆烯反应，其中氮充当氢供体，而炔键末端上的烷基取代导致新的，容易的环化成α 2-亚烷基亚吡咯烷。
• VIOLA, A.;LOCKE, J. S., J. CHEM. SOC. CHEM. COMMUN., 1984, N 21, 1429-1431
  作者：VIOLA, A.、LOCKE, J. S.

  DOI：——

  日期：——
• Amine Oxidase Inhibitors
  申请人：Sayre Lawrence M.

  公开号：US20080199933A1

  公开（公告）日：2008-08-21

  A therapeutic agent for selectively inhibiting amine oxidases associated diseases and conditions in humans includes at least one compound selected from the group consisting of propargylamines, polypropargylamines, homopropargylamines, 4-substituted-2-butynylamines, 2- and 3-halloallylamines, pyrroline derivatives, cycloalkenyl branched primary amines, propargyl diamines, homopropargyl amines and diamines, allenyl amines and diamines, chloroallyl diamines, lysyne analogues, β-haloamines, RF-substituted amines, RC 1 -substituted amines, and R3Si substituted amines.
• US9161922B2
  申请人：——

  公开号：US9161922B2

  公开（公告）日：2015-10-20
• Acetylenes as potential antarafacial components in concerted reactions. Formation of pyrroles from thermolyses of propargyl amines, of a dihydrofuran from a propargylic ether, and of an ethylidenepyrrolidine from a .beta.-amino acetylene
  作者：Alfred Viola、John J. Collins、Nicholas Filipp、John S. Locke

  DOI：10.1021/jo00071a015

  日期：1993.9

  A thermal cyclization of acetylenic compounds provides evidence for the ability of acetylenic links to act as antarafacial components in [2 + 2] processes. The cyclization competes with the normally favored acetylenic retro-ene reaction. Propargylic amines, without substituents whose presence would hinder a tight cyclic transition state, yield intermediate pyrrolines whose subsequent hydrogen elimination affords pyrroles in small amounts. The same process in 2-ethynyltetrahydropyran affords 8-oxabicyclo[3.2.1]octane in 35% yield. A related thermal reaction of N-methyl-3-hexyn-1-amine provides a quantitative transformation to N-methyl-2-ethylidenepyrrolidine in a nominal [2s + 2a + 2s + 2s] Mobius process, wherein the acetylenic unit is the antarafacial component. Evidence for concertedness in these reactions is discussed.