(3R,E)-2-(4-hydroxybut-2-enyl)-3-methylcycloheptanone | 1206765-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,E)-2-(4-hydroxybut-2-enyl)-3-methylcycloheptanone
• 英文别名: (2S,3R)-2-[(E)-4-hydroxybut-2-enyl]-3-methylcycloheptan-1-one
• CAS: 1206765-90-3
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: YILCMOSSYFQYEG-ZJRFNNFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环氧丁烯 、 2-环庚烯-1-酮 、 Dimethylzinc 在 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 、 copper(II) bis(trifluoromethanesulfonate) 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (3R)-2-(4-hydroxybut-2-enyl)-3-methylcycloheptanone 、 (3R,Z)-2-(4-hydroxybut-2-enyl)-3-methylcycloheptanone 、 (3R,E)-2-(4-hydroxybut-2-enyl)-3-methylcycloheptanone
  参考文献：
  名称：

  Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes

  摘要：

  An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cls/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.

  DOI：

  10.1021/ol9027682

文献信息

• Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes
  作者：Matthias Welker、Simon Woodward、Alexandre Alexakis

  DOI：10.1021/ol9027682

  日期：2010.2.5

  An opening of vinyl oxiranes has been accomplished with Zn and Al enolates resulting from asymmetric conjugate addition reactions on cyclic enones. This novel tandem procedure affords the adducts in moderate to good yields, enantioselectivities up to 98%, and moderate to good cls/trans selectivities. This provides potentially useful synthetic substrates to prepare complex bicyclic compounds.