2-(7-Azido-hept-2-ynyloxy)-tetrahydro-pyran | 856015-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(7-Azido-hept-2-ynyloxy)-tetrahydro-pyran
• 英文别名: 2-(7-azidohept-2-ynoxy)oxane
• CAS: 856015-55-9
• 化学式: C₁₂H₁₉N₃O₂
• 分子量: 237.302
• InChiKey: RDCHPAOZFLAEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  67.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(7-Azido-hept-2-ynyloxy)-tetrahydro-pyran 在 Lindlar's catalyst 盐酸 、 manganese(IV) oxide 、 氢气 、 sodium sulfate 、 (2S,5S)-2,5-bis[tert-butyl(dimethyl)silyloxymethyl]pyrrolidine 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 53.0h， 生成 1,2,3,4,4a,8,9,10-octahydro-pyrido[1,2-a]quinolin-7-one
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s
• 作为产物：
  描述：

  2-((7-bromohept-2-yn-1-yl)oxy)tetrahydro-2H-pyran 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以95%的产率得到2-(7-Azido-hept-2-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  A Formal [3 + 3] Cycloaddition Reaction. 5. An Enantioselective Intramolecular Formal Aza-[3 + 3] Cycloaddition Reaction Promoted by Chiral Amine Salts

  摘要：

  A detailed account on chiral secondary amine salt promoted enantioselective intramolecular formal aza-[3 + 3] cycloadditions is described here for the first time. The dependence of enantioselectivity on the structural feature of these chiral amines is thoroughly investigated. This study also reveals a very interesting reversal of the stereochemistry in the respective cycloadducts obtained using C-1- and C-2-symmetric amine salts. In addition, the influence of solvents, counteranions, and temperatures on the enantioselectivity is described, and a unified mechanistic model based on experimental results as well as semiempirical calculations is proposed.

  DOI：

  10.1021/jo050171s