(S,E)-1-methyl-2-(2-methylundeca-1,4-dien-3-yl)benzene | 1005414-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,E)-1-methyl-2-(2-methylundeca-1,4-dien-3-yl)benzene
• 英文别名: 1-methyl-2-[(3S,4E)-2-methylundeca-1,4-dien-3-yl]benzene
• CAS: 1005414-07-2
• 化学式: C₁₉H₂₈
• 分子量: 256.431
• InChiKey: LWNVRFLAJJSFKV-MDNBWPLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  diethyl [(E)-2-methyl-3-(2-methylphenyl)prop-2-enyl] phosphate 、 1-辛炔 在 NHC-Ag(I) complex 、 CuCl₂*2H₂O 二异丁基氢化铝 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 5.0h， 以87%的产率得到(S,E)-1-methyl-2-(2-methylundeca-1,4-dien-3-yl)benzene
  参考文献：
  名称：

  Highly Site- and Enantioselective Cu-Catalyzed Allylic Alkylation Reactions with Easily Accessible Vinylaluminum Reagents

  摘要：

  An efficient method for catalytic asymmetric allylic alkylation (AAA) of allylic phosphates with vinylaluminum reagents is reported. The vinylmetal reagents are prepared by reaction of commercially available DIBAL-H and a terminal alkyne. The resulting vinylaluminum reagent can be used directy, without isolation or purification. AAA reactions are promoted in the presence of 0.5-2.5 mol % of a readily available chiral N-heterocyclic carbene (NHC) complex and 1-5 mol % commercially available and air stable Cu salt (CUCl2-2H(2)O). The desired products are typically obtained within 2-12 h in 74% to 95% isolated yield, 77% to >98% ee, and in >98% E selectivity: >98% S(N)2' selectively is obtained in all but one instance (90%). The hydroalummation/catalytic AAA sequence can be performed in a single vessel, on gram scale.

  DOI：

  10.1021/ja0782192

文献信息

• Highly Site- and Enantioselective Cu-Catalyzed Allylic Alkylation Reactions with Easily Accessible Vinylaluminum Reagents
  作者：Yunmi Lee、Katsuhiro Akiyama、Dennis G. Gillingham、M. Kevin Brown、Amir H. Hoveyda

  DOI：10.1021/ja0782192

  日期：2008.1.1

  An efficient method for catalytic asymmetric allylic alkylation (AAA) of allylic phosphates with vinylaluminum reagents is reported. The vinylmetal reagents are prepared by reaction of commercially available DIBAL-H and a terminal alkyne. The resulting vinylaluminum reagent can be used directy, without isolation or purification. AAA reactions are promoted in the presence of 0.5-2.5 mol % of a readily available chiral N-heterocyclic carbene (NHC) complex and 1-5 mol % commercially available and air stable Cu salt (CUCl2-2H(2)O). The desired products are typically obtained within 2-12 h in 74% to 95% isolated yield, 77% to >98% ee, and in >98% E selectivity: >98% S(N)2' selectively is obtained in all but one instance (90%). The hydroalummation/catalytic AAA sequence can be performed in a single vessel, on gram scale.