4-methyl-N-[3-phenyl-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)propyl]benzenesulfonamide | 1046826-32-7

• 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: 4-methyl-N-[3-phenyl-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)propyl]benzenesulfonamide
• CAS: 1046826-32-7
• 化学式: C₂₃H₃₁NO₄S
• 分子量: 417.569
• InChiKey: KRFFPWFIAIDTAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4,4,5,5-tetramethyl-1,3-dioxolane 、 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 在 air 、 Dimethylzinc 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 6.75h， 以15%的产率得到4-methyl-N-[3-phenyl-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)propyl]benzenesulfonamide
  参考文献：
  名称：

  Conjugate addition reaction of THF-2-yl radical with α,β-unsaturated N-tosyl imines using a dimethylzinc–air initiator

  摘要：

  The reaction of tetrahydrofuran-2-yl radical, generated directly from THF by the action of dimethylzinc-air, with of alpha,beta-unsaturated N-tosyl aldimines was demonstrated to proceed preferentially in a conjugate addition manner to give 2-(3-hydroxyalkyl)- or 2-(3-aminoalkyl)tetrahydrofurans in good yield. The slow addition of the enimines and the use of dimethylzinc, rather than diethylzinc or triethylborane, were found to be the keys for the efficiency of the THF conjugate addition. The observed chemoselectivity could be rationalized by the larger coefficient of LUMO at the corresponding reaction site of the enimine (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.069