(E)-2-Methyl-3-[(2R,3R)-3-phenyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-acrylic acid methyl ester | 196958-89-1

• 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)-2-Methyl-3-[(2R,3R)-3-phenyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-acrylic acid methyl ester
• CAS: 196958-89-1
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: GNMYWOCRMPZDHU-WBEQDMNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Methyl-3-[(2R,3R)-3-phenyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-acrylic acid methyl ester 在 bis(η3-allyl-μ-chloropalladium(II)) 马来酸酐 、 甲酸 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.6h， 以18%的产率得到(E)-(S)-2-Methyl-5-phenyl-5-(toluene-4-sulfonylamino)-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group

  摘要：

  The palladium-catalyzed reduction of various N-arenesulfonylaziridines bearing alpha,beta-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in detail. In all cases examined, (Z)-alpha,beta-enoates, (E)-alpha,beta-enoates, and (E)-beta,gamma-enoates bearing amino functionality at the delta-position were obtained. The formation of these three reduction products was taken as an indication that palladium-catalyzed isomerization occurs prior to the reduction step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00817-x
• 作为产物：
  描述：

  3-苯基缩水甘油 在 sodium azide 、 氯化铵 、 三乙胺 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 反应 13.0h， 生成 (E)-2-Methyl-3-[(2R,3R)-3-phenyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group

  摘要：

  The palladium-catalyzed reduction of various N-arenesulfonylaziridines bearing alpha,beta-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in detail. In all cases examined, (Z)-alpha,beta-enoates, (E)-alpha,beta-enoates, and (E)-beta,gamma-enoates bearing amino functionality at the delta-position were obtained. The formation of these three reduction products was taken as an indication that palladium-catalyzed isomerization occurs prior to the reduction step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00817-x