5-(3-(tert-butyldimethylsilyloxy)-4-methylpent-4-enyl)-3-methoxycyclopent-2-enone | 1354552-41-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-(3-(tert-butyldimethylsilyloxy)-4-methylpent-4-enyl)-3-methoxycyclopent-2-enone
• 英文别名: 5-[3-[Tert-butyl(dimethyl)silyl]oxy-4-methylpent-4-enyl]-3-methoxycyclopent-2-en-1-one
• CAS: 1354552-41-2
• 化学式: C₁₈H₃₂O₃Si
• 分子量: 324.536
• InChiKey: VJYGXJCEOLRIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-(tert-butyldimethylsilyloxy)-4-methylpent-4-enyl)-3-methoxycyclopent-2-enone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 5-(3-hydroxy-4-methylpent-4-enyl)-3-methoxycyclopent-2-enone
  参考文献：
  名称：

  Stereoselective α-Quaternization of 3-Methoxycycloalk-2-enones via 1,4-Diastereoinduction of Alkoxy Dienolates

  摘要：

  The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the alpha-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.

  DOI：

  10.1021/jo2022789
• 作为产物：
  描述：

  3-甲氧基-2-环戊烯-1-酮 、 (3RS)-tert-butyl[(5-iodo-2-methylpent-1-en-3-yl)oxy]dimethylsilane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以77%的产率得到5-(3-(tert-butyldimethylsilyloxy)-4-methylpent-4-enyl)-3-methoxycyclopent-2-enone
  参考文献：
  名称：

  Stereoselective α-Quaternization of 3-Methoxycycloalk-2-enones via 1,4-Diastereoinduction of Alkoxy Dienolates

  摘要：

  The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the alpha-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.

  DOI：

  10.1021/jo2022789

文献信息

• Stereoselective α-Quaternization of 3-Methoxycycloalk-2-enones via 1,4-Diastereoinduction of Alkoxy Dienolates
  作者：Gamal A. I. Moustafa、Yasumasa Kamada、Tetsuaki Tanaka、Takehiko Yoshimitsu

  DOI：10.1021/jo2022789

  日期：2012.1.20

  The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the alpha-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.