(E)-2,4,6-triisopropyl-N-[(E)-3-(naphthalen-1-yl)allylidene]benzenesulfonamide | 824984-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2,4,6-triisopropyl-N-[(E)-3-(naphthalen-1-yl)allylidene]benzenesulfonamide
• 英文别名: (NE)-N-[(E)-3-naphthalen-1-ylprop-2-enylidene]-2,4,6-tri(propan-2-yl)benzenesulfonamide
• CAS: 824984-19-2
• 化学式: C₂₈H₃₃NO₂S
• 分子量: 447.642
• InChiKey: YATZDONUVVTXRY-IRTGNHEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二异丙基锌 、 (E)-2,4,6-triisopropyl-N-[(E)-3-(naphthalen-1-yl)allylidene]benzenesulfonamide 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 4.0h， 生成 (-)-4-methyl-3-(naphthalen-1-yl)pentan-1-ol 、 (-)-4-methyl-3-(naphthalen-1-yl)pentan-1-ol
  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：

  2,4,6-三异丙基苯磺胺 、 3-(1-naphthyl)acrolein 在 硅酸四乙酯 作用下， 反应 12.0h， 以71%的产率得到(E)-2,4,6-triisopropyl-N-[(E)-3-(naphthalen-1-yl)allylidene]benzenesulfonamide
  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.