(E)-N-[(E)-3-(furan-2-yl)allylidene]-2,4,6-triisopropylbenzenesulfonamide

• 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: (E)-N-[(E)-3-(furan-2-yl)allylidene]-2,4,6-triisopropylbenzenesulfonamide
• 英文别名: (NE)-N-[(E)-3-(furan-2-yl)prop-2-enylidene]-2,4,6-tri(propan-2-yl)benzenesulfonamide
• 化学式: C₂₂H₂₉NO₃S
• 分子量: 387.543
• InChiKey: QUGAVTCILASXAN-KWOBAQOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 (E)-N-[(E)-3-(furan-2-yl)allylidene]-2,4,6-triisopropylbenzenesulfonamide 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 {1(S)-[((2S)-diphenylphosphinomethyl)pyrrolidine-1-carbonyl]-2-methylpropyl}carbamic acid tert-butyl ester aluminum oxide 、 sodium tetrahydroborate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成 3-(2-Furyl)-1-pentanol 、 3-(2-Furyl)-1-pentanol
  参考文献：
  名称：

  Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-2,4,6-Triisopropylphenylsulfonylaldimines with Use of N-Boc-l-Val-Connected Amidophosphane-Copper(I) Catalyst

  摘要：

  Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-BOC-L-valine-connected amidophosphane 5a-Cu-(MeCN)(4)BF4 in the presence of 4 Angstrom MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.

  DOI：

  10.1021/jo0484225
• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 2,4,6-三异丙基苯磺胺 在 硅酸四乙酯 作用下， 反应 12.0h， 以53%的产率得到(E)-N-[(E)-3-(furan-2-yl)allylidene]-2,4,6-triisopropylbenzenesulfonamide
  参考文献：
  名称：

  Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-2,4,6-Triisopropylphenylsulfonylaldimines with Use of N-Boc-l-Val-Connected Amidophosphane-Copper(I) Catalyst

  摘要：

  Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-BOC-L-valine-connected amidophosphane 5a-Cu-(MeCN)(4)BF4 in the presence of 4 Angstrom MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.

  DOI：

  10.1021/jo0484225

文献信息

• Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated <i>N</i>-2,4,6-Triisopropylphenylsulfonylaldimines with Use of <i>N</i>-Boc-<scp>l</scp>-Val-Connected Amidophosphane-Copper(I) Catalyst
  作者：Takahiro Soeta、Masami Kuriyama、Kiyoshi Tomioka

  DOI：10.1021/jo0484225

  日期：2005.1.1

  Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-BOC-L-valine-connected amidophosphane 5a-Cu-(MeCN)(4)BF4 in the presence of 4 Angstrom MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.