2-Pentenedioic acid, 4-cyano-4-methyl-, diethyl ester, (Z)- | 173593-82-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Pentenedioic acid, 4-cyano-4-methyl-, diethyl ester, (Z)-
• 英文别名: diethyl (Z)-2-cyano-2-methyl-3-pentenedioate
• CAS: 173593-82-3
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: INZACHTXIDXQNS-SREVYHEPSA-N

物化性质

• 沸点：
  328.5±37.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  76.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氰基丙酸乙酯 、 丙炔酸乙酯 在 [RuH2(PPh3)4] 作用下， 以 四氢呋喃 为溶剂， 生成 diethyl (E)-2-cyano-2-methyl-3-pentenedioate 、 2-Pentenedioic acid, 4-cyano-4-methyl-, diethyl ester, (Z)-
  参考文献：
  名称：

  钌催化活化腈的羟醛和迈克尔反应

  摘要：

  Catalyze par RuH 2 (PPh 3 ) 4 des reactors de cyanoesters, dinitriles et du benzonitrile avec des aldehydes, enaldehydes, cetones et enones pour donner les produits d'aldolisation et d'addition de Michael, 通讯员

  DOI：

  10.1021/ja00197a073

文献信息

• Ruthenium-catalyzed aldol and Michael reactions of nitriles. Carbon-carbon bond formation by .alpha.-C-H activation of nitriles.
  作者：Shun-Ichi Murahashi、Takeshi Naota、Hiroshi Taki、Masahiko Mizuno、Hikaru Takaya、Sanshiro Komiya、Yuji Mizuho、Naohiko Oyasato、Makiko Hiraoka

  DOI：10.1021/ja00155a008

  日期：1995.12

  The ruthenium(II)-catalyzed reaction of nitriles with carbonyl compounds proceeds highly efficiently under neutral and mild conditions to give alpha,beta-unsaturated nitriles. Under similar reaction conditions, nitriles react with olefins bearing electron-withdrawing groups to give the corresponding Michael adducts. The efficiency of the reaction is illustrated by the selective additions to alpha,beta-unsaturated aldehydes and acetylenes bearing electron-withdrawing groups, which are difficult to perform using conventional bases. Chemoselective aldol and Michael reactions of nitriles can be performed in the presence of other active methylene compounds. Tandem Michael and Michael-aldol condensations of nitriles 30 can be performed with high diastereoselectivity. These reactions can be rationalized by assuming oxidative addition of ruthenium(0) to the alpha=C-H bond of nitriles and subsequent insertions to carbonyl compounds or olefins. As the key intermediates and active catalysts hydrido(N-bonded enolato)ruthenium(II) complexes, mer-RuH(NCCHCO(2)R)(NCCH(2)CO(2)R)(PPh(3))(3) (R = Me (41a), Et (41b), n-Bu (41c) have been upon treatment of RuH2(PPh(3))(4) (3) or RuH(C2H4)(PPh(3))(2)(PPh(2)C(6)H(4)) (4) with alkyl cyanoacetates. Kinetic study of the catalytic aldol reaction of ethyl cyanoacetate with benzaldehyde indicates that the rate-determining step reaction of enolato complex 41 with aldehydes.