3-((E)-6-Hydroxy-hex-4-enylamino)-cyclohex-2-enone | 856015-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((E)-6-Hydroxy-hex-4-enylamino)-cyclohex-2-enone
• CAS: 856015-64-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: VWUMALSGCXMGTH-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((E)-6-Hydroxy-hex-4-enylamino)-cyclohex-2-enone 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以58%的产率得到(E)-6-(3-Oxo-cyclohex-1-enylamino)-hex-2-enal
  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-((6-bromohex-2-yn-1-yl)oxy)tetrahydro-2H-pyran 在 lithium aluminium tetrahydride 、 sodium azide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 6.0h， 生成 3-((E)-6-Hydroxy-hex-4-enylamino)-cyclohex-2-enone
  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