4-acetoxy-2,5,5-trimethyl-2-hexene | 223140-33-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-acetoxy-2,5,5-trimethyl-2-hexene
• 英文别名: 2,2,5-Trimethylhex-4-en-3-yl acetate
• CAS: 223140-33-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: FDNQTMDEYHTADN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 4-acetoxy-2,5,5-trimethyl-2-hexene 以 二氯甲烷 为溶剂， 生成 (3S*,4S*)-4-acetoxy-2,5,5-trimethyl-3-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-1-hexene 、 (3R*,4S*)-4-acetoxy-2,5,5-trimethyl-3-(4'-phenyl-1',2',4'-triazolidine-3',5'-dion-1'-yl)-1-hexene
  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
• 作为产物：
  描述：

  3-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 16.0h， 生成 4-acetoxy-2,5,5-trimethyl-2-hexene
  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

文献信息

• Regio- and Diastereoselective Ene Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione with Chiral Allylic Alcohols and Their Derivatives
  作者：Ay-Hua Gau、Guey-Liang Lin、Biing-Jiun Uang、Fen-Ling Liao、Sue-Lein Wang

  DOI：10.1021/jo980835g

  日期：1999.4.1

  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).