(2R*,4S*)-4-acetoxy-5,5-dimethyl-3-methylene-2-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-hexane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2R*,4S*)-4-acetoxy-5,5-dimethyl-3-methylene-2-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-hexane
• 英文别名: [(3S,5R)-5-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-2,2-dimethyl-4-methylidenehexan-3-yl] acetate
• 化学式: C₁₉H₂₅N₃O₄
• 分子量: 359.425
• InChiKey: FJDWTAWZLVZPHH-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (2R*,4S*)-4-acetoxy-5,5-dimethyl-3-methylene-2-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-hexane
  参考文献：
  名称：

  Regio- and Diastereoselective Ene Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione with Chiral Allylic Alcohols and Their Derivatives

  摘要：

  Chiral allylic alcohols la-e reacted with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in CH2Cl2 to produce 3-amino-1-alken-4-ols 2 and 3 in 78-89% yields, with 68-90% diastereomeric excess (de) in favor of the three isomer. Chiral allylic ethers If,g and acetates Ih,i gave similar yields but lower de (34-66%). Reaction of allylic alcohols 6a-e with PTAD in CH2Cl2 produced 1,3-regioisomers 7 and 8 exclusively in 33-65% yields without apparent diastereoselectivity, except when R-1 was a Bu-t group, in which case only syn product 7 was formed. However, when 6a or 6c was subjected to reaction with PTAD in a polar solvent, up to 88% de was observed. Reaction of allylic ethers 6f,g and acetates 6h,i with PTAD in CH2Cl2 also produced 7 and 8 exclusively with improved yields (56-96%) and diastereoselectivity (50-100% de in favor of the syn isomer).

  DOI：

  10.1021/jo980835g