β-Butyl-hydrozimtsaeure-anilid | 15954-54-8

• 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: β-Butyl-hydrozimtsaeure-anilid
• 英文别名: N,3-diphenylheptanamide
• CAS: 15954-54-8
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: CWAVWBGLSANVPN-UHFFFAOYSA-N

物化性质

• 沸点：
  463.3±24.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-Phenyl-2-trimethylsilanyl-heptanoic acid phenylamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 β-Butyl-hydrozimtsaeure-anilid
  参考文献：
  名称：

  Charge-directed conjugate addition reactions of silylated .alpha.,.beta.-unsaturated amidate anions

  摘要：

  A variety of N-substituted alpha-silylated-alpha,beta-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. Beta-Substituted acceptors were found to react only with reactive organolithium reagents while a beta,beta-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.

  DOI：

  10.1021/jo00078a028

文献信息

• “contra-Michael” Addition of Alkyllithiums to Silicon- and Phenyl-substituted α,β-Unsaturated Amides in the Presence of<i>t</i>-BuOK
  作者：Tomoko Hinago、Nana Teshima、Satoko Kenmoku、Tiyako Kamata、Nahoko Terauchi、Nao Chiba、Chikako Satoh、Aya Nakamura、Morio Asaoka

  DOI：10.1246/cl.2007.54

  日期：2007.1

  Carbolithiation of 3-(trimethylsilyl)acrylamide and cinnamamide derivatives gave the corresponding 3-substituted (Michael) and/or 2-substituted (contra-Michael) adducts. The regioselectivity depends on the nature of alkyllithium reagents. In the carbolithiation with n-alkyllithiums, the presence of t-BuOK caused dramatic change of the addition mode and the contra-Michael adducts were obtained exclusively.

  3-(三甲基硅基)丙烯酰胺和肉桂酰胺衍生物的碳锂化反应产生了相应的3-取代物（迈克尔加成物）和/或2-取代物（反迈克尔加成物）。区域选择性依赖于烃锂试剂的性质。在与正烷基锂的碳锂化反应中，存在t-BuOK导致了加成模式的显著变化，反迈克尔加成物被独占性地获得。
• Conjugate Addition of RMgX–3MeLi to α,β-Unsaturated Amides and α,β-Unsaturated Carboxylic Acids
  作者：Mikiko Kikuchi、Satomi Niikura、Nao Chiba、Nahoko Terauchi、Morio Asaoka

  DOI：10.1246/cl.2007.736

  日期：2007.6.5

  In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in g...

  在 3 当量的 MeLi 存在下，各种格氏试剂与仲 α,β-不饱和酰胺和 α,β-不饱和羧酸反应，得到相应的迈克尔加合物。