(E)-N,N-diethyl-2-methyl-2-butenamide | 133217-97-7

• 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: (E)-N,N-diethyl-2-methyl-2-butenamide
• 英文别名: 2-Butenamide, N,N-diethyl-2-methyl-, (E)-；(E)-N,N-diethyl-2-methylbut-2-enamide
• CAS: 133217-97-7
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: FKTDBDLCSXPFJU-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-diethyl-2-methyl-2-butenamide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到(2R*,3S*)-N,N-diethyl-2,3-dimethyloxirane carboxamide
  参考文献：
  名称：

  Opposite π-Face Selectivity for the DMD and m-CPBA Epoxidations of Chiral 2,2-Dimethyloxazolidine Derivatives of Tiglic Amides:  Control by Steric Interactions versus Hydrogen Bonding

  摘要：

  A high extent but opposite sense in the diastereoselectivity has been observed for the DMD and m-CPBA epoxidations of the optically active tiglic amides (S)-1 with 2,2-dimethyloxazolidines as chiral auxiliaries, This unprecedented reversed pi-facial differentiation for these two peroxidic oxidants is rationalized in terms of like (lk) and unlike (ul) transition structures: For DMD, steric interactions dominate, such that the unlike transition structure is favored, while for m-CPBA, hydrogen bonding effects overcome these steric repulsions and the like one is preferred.

  DOI：

  10.1021/ol990405s
• 作为产物：
  描述：

  (Z)-N,N-diethylangelamide 在 偶氮二异丁腈 、 二苯二硫醚 作用下， 以 苯 为溶剂， 反应 5.0h， 以87%的产率得到(E)-N,N-diethyl-2-methyl-2-butenamide
  参考文献：
  名称：

  A Facile Conversion of (Z)-2-Alkenoic Esters into the (E)-Isomers with Diphenyl Disulfide

  摘要：

  研究表明，二苯基二硫化物是一种高效催化剂，可在沸腾的四氢呋喃中将(Z)-2-烯酸酯异构化为(E)-2-烯酸酯。

  DOI：

  10.1055/s-1990-27110

文献信息

• Rh^III‐Catalyzed Oxidative Olefination of Vinylic CH Bonds: Efficient and Selective Access to Di‐unsaturated α‐Amino Acid Derivatives and Other Linear 1,3‐Butadienes
  作者：Tatiana Besset、Nadine Kuhl、Frederic W. Patureau、Frank Glorius

  DOI：10.1002/chem.201101340

  日期：2011.6.20

  get‐together! A RhIII‐catalyzed oxidative cross‐coupling of different olefins was developed, resulting in the formation of valuable linear butadiene products and especially di‐unsaturated α‐amino acid derivatives. 1,1‐Di‐, 1,2‐di‐, and 1,1,2‐trisubstituted olefins could be coupled with styrenes and acrylates. In these reactions, remarkably high levels of chemo‐, regio‐, and stereoselectivity were obtained

  烯烃在一起！开发了Rh III催化的不同烯烃的氧化交叉偶联反应，从而形成了有价值的线性丁二烯产物，尤其是二不饱和α-氨基酸衍生物。1,1-二，1,2-二和1,1,2-三取代的烯烃可以与苯乙烯和丙烯酸酯偶联。在这些反应中，获得了很高的化学，区域和立体选择性，这使其成为一种有价值的合成工具。
• MIYATA, OKIKO;SHINADA, TETSURO;NINOMIYA, ICHIYA;NAITO, TAKEAKI, SYNTHESIS,(1990) N2, C. 1123-1125
  作者：MIYATA, OKIKO、SHINADA, TETSURO、NINOMIYA, ICHIYA、NAITO, TAKEAKI

  DOI：——

  日期：——
• Opposite π-Face Selectivity for the DMD and <i>m</i>-CPBA Epoxidations of Chiral 2,2-Dimethyloxazolidine Derivatives of Tiglic Amides:  Control by Steric Interactions versus Hydrogen Bonding
  作者：Waldemar Adam、Aurelia Pastor、Karl Peters、Eva-Maria Peters

  DOI：10.1021/ol990405s

  日期：2000.4.1

  A high extent but opposite sense in the diastereoselectivity has been observed for the DMD and m-CPBA epoxidations of the optically active tiglic amides (S)-1 with 2,2-dimethyloxazolidines as chiral auxiliaries, This unprecedented reversed pi-facial differentiation for these two peroxidic oxidants is rationalized in terms of like (lk) and unlike (ul) transition structures: For DMD, steric interactions dominate, such that the unlike transition structure is favored, while for m-CPBA, hydrogen bonding effects overcome these steric repulsions and the like one is preferred.
• A Facile Conversion of (<i>Z</i>)-2-Alkenoic Esters into the (<i>E</i>)-Isomers with Diphenyl Disulfide
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1055/s-1990-27110

  日期：——

  Diphenyl disulfide is shown to be an efficient catalyst for the isomerization of (Z)-2-alkenoic esters to (E)-2-alkenoic esters in boiling tetrahydrofuran.

  研究表明，二苯基二硫化物是一种高效催化剂，可在沸腾的四氢呋喃中将(Z)-2-烯酸酯异构化为(E)-2-烯酸酯。