2-hydroxy-1-phenyl-3-vinylhexan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-1-phenyl-3-vinylhexan-1-one
• 英文别名: 3-ethenyl-2-hydroxy-1-phenylhexan-1-one
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: FYCIVTOJARDYGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 在 正丙胺 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole 、 水 、 diethylzinc 、 sodium formate 、 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 (2S,3S)-2-hydroxy-1-phenyl-3-vinylhexan-1-one 、 2-hydroxy-1-phenyl-3-vinylhexan-1-one
  参考文献：
  名称：

  An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones

  摘要：

  An Ir/Zn dual catalysis has been developed for the enantio- and diastereodivergent alpha-allylation of unprotected alpha-hydroxyketones under mild conditions, in the absence of any additional base. The cooperative action of a chiral iridium complex derived from phosphoramidites and a chiral Zn-ProPhenol complex is most likely responsible for its high reactivity, excellent enantioselectivity (up to >99% ee), and good diastereoselectivity (up to >20:1 dr). All four product stereoisomers could be prepared from the same set of starting materials and under identical conditions by simple selection of appropriate catalyst combinations.

  DOI：

  10.1021/jacs.6b06156

文献信息

• An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones
  作者：Xiaohong Huo、Rui He、Xiao Zhang、Wanbin Zhang

  DOI：10.1021/jacs.6b06156

  日期：2016.9.7

  An Ir/Zn dual catalysis has been developed for the enantio- and diastereodivergent alpha-allylation of unprotected alpha-hydroxyketones under mild conditions, in the absence of any additional base. The cooperative action of a chiral iridium complex derived from phosphoramidites and a chiral Zn-ProPhenol complex is most likely responsible for its high reactivity, excellent enantioselectivity (up to >99% ee), and good diastereoselectivity (up to >20:1 dr). All four product stereoisomers could be prepared from the same set of starting materials and under identical conditions by simple selection of appropriate catalyst combinations.