2-(3-Methylbut-2-enyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one | 1446140-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(3-Methylbut-2-enyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one
• 英文别名: 2-(3-methylbut-2-enyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one
• CAS: 1446140-18-6
• 化学式: C₁₈H₂₂O
• 分子量: 254.372
• InChiKey: UMRKQWNNQNNCON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  梨醇酯 在 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2-(3-Methylbut-2-enyl)-2-prop-2-enyl-3,4-dihydronaphthalen-1-one
  参考文献：
  名称：

  Development of Asymmetric Deacylative Allylation

  摘要：

  Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.

  DOI：

  10.1021/jo400793a

文献信息

• Development of Asymmetric Deacylative Allylation
  作者：Alexander J. Grenning、Christie K. Van Allen、Tapan Maji、Simon B. Lang、Jon A. Tunge

  DOI：10.1021/jo400793a

  日期：2013.7.19

  Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.