3-Hexyn-1-yl tosylate | 60093-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Hexyn-1-yl tosylate
• CAS: 60093-50-7
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: HOUCBYWEQUJWDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-Hexyn-1-yl tosylate 25.0~400.0 ℃ 、6.67 kPa 条件下， 反应 96.0h， 生成 1-methyl-2-ethylidenepyrrolidine
  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
• 作为产物：
  描述：

  3-已炔-1-醇 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 3-Hexyn-1-yl tosylate
  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