[morpholin-4-yl-(4-nitro-phenyl)-methylene]-malonic acid diethyl ester | 38238-95-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [morpholin-4-yl-(4-nitro-phenyl)-methylene]-malonic acid diethyl ester
• CAS: 38238-95-8
• 化学式: C₁₈H₂₂N₂O₇
• 分子量: 378.382
• InChiKey: TVJDGIOXFIEAGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  108.21
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  吗啉 、 2-[(4-Nitro-phenyl)-trifluoromethanesulfonyloxy-methylene]-malonic acid diethyl ester 以 乙腈 为溶剂， 生成 [morpholin-4-yl-(4-nitro-phenyl)-methylene]-malonic acid diethyl ester
  参考文献：
  名称：

  Triflate/Mesylate Ratios and Competing C−O and S−O Bond Cleavages in Nucleophilic Vinylic Substitution

  摘要：

  In an attempt to develop the k(OTf)/K-OMs ratio as a mechanistic tool for the ''addition-elimination'' route in nucleophilic vinylic substitution, several pairs of vinyl mesylates and triflates were prepared. Whereas reactions of ArC(LG)=C(CO(2)Et)(2) (LG = OTf, OMs) with piperidine and morpholine in MeCN or THF gave the normal substitution product with k(OTf)/k(OMs) ratios of 4.3-10.6, the reaction of the mesylates, Ar = p-O2NC6H4, and of PhC(OMs)=C(Me)CN with MeS(-) gave a ketone via an S-O bond cleavage. A related mesityl-substituted tosylate also reacted with p-MeC(6)H(4)X(-) (X = O, S) via an S-O bond cleavage. Hence, k(OTf)/k(OMs) ratios cannot be used as a general mechanistic tool. Several reactivity ratios in vinylic substitution are briefly discussed.

  DOI：

  10.1021/jo961108t