1,3-Dimethyl-6-[(Z)-7-(tetrahydro-pyran-2-yloxy)-hept-5-enylamino]-1H-pyrimidine-2,4-dione | 878206-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-Dimethyl-6-[(Z)-7-(tetrahydro-pyran-2-yloxy)-hept-5-enylamino]-1H-pyrimidine-2,4-dione
• CAS: 878206-52-1
• 化学式: C₁₈H₂₉N₃O₄
• 分子量: 351.446
• InChiKey: UFXPLOVYLRHXBL-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.49
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-6-[(Z)-7-(tetrahydro-pyran-2-yloxy)-hept-5-enylamino]-1H-pyrimidine-2,4-dione 在 manganese(IV) oxide 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 (Z)-7-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-ylamino)-hept-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-((7-bromohept-2-yn-1-yl)oxy)tetrahydro-2H-pyran 在 Lindlar's catalyst sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 1,3-Dimethyl-6-[(Z)-7-(tetrahydro-pyran-2-yloxy)-hept-5-enylamino]-1H-pyrimidine-2,4-dione
  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