(+/-)-syn-5-hydroxy-2,2,4-trimethylnonan-3-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-syn-5-hydroxy-2,2,4-trimethylnonan-3-one
• 英文别名: (4R,5S)-5-hydroxy-2,2,4-trimethylnonan-3-one
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: WRQOXZAJRURWGR-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-syn-5-hydroxy-2,2,4-trimethylnonan-3-one 在 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到(E)-2,2,4-trimethylnon-4-en-3-one
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Coupling Reactions in Exceptionally Hindered Contexts

  摘要：

  Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R-1 = Me). This technique complements other methods,and enables the preparation of enones outside of the scope of current olefination methodology.

  DOI：

  10.1021/ol800099a
• 作为产物：
  描述：

  正戊醛 、 2-溴-4,4-二甲基-3-戊酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以85%的产率得到(+/-)-syn-5-hydroxy-2,2,4-trimethylnonan-3-one
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Coupling Reactions in Exceptionally Hindered Contexts

  摘要：

  Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R-1 = Me). This technique complements other methods,and enables the preparation of enones outside of the scope of current olefination methodology.

  DOI：

  10.1021/ol800099a

文献信息

• SmI₂-Promoted Reformatsky-Type Coupling Reactions in Exceptionally Hindered Contexts
  作者：Brian A. Sparling、Ryan M. Moslin、Timothy F. Jamison

  DOI：10.1021/ol800099a

  日期：2008.3.1

  Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R-1 = Me). This technique complements other methods,and enables the preparation of enones outside of the scope of current olefination methodology.