(Z)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide | 134485-67-9

• 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: (Z)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide
• 英文别名: (Z)-N,N-diisopropyl-2-methyl-3-phenylacrylamide
• CAS: 134485-67-9
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: WJAGIRFDOAXSBG-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide 在 palladium on activated charcoal 氘 作用下， 以 重水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 (R*,R*)-2,3-dideuterio-N,N-diisopropyl-2-methyl-3-phenylpropanamide
  参考文献：
  名称：

  Complex induced proximity effects: .beta.-lithiations of carboxamides

  摘要：

  The R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2,3-dideuterio-2-methyl-3-phenylpropanamide (5,6) have been used to investigate the diastereoselectivity of the beta-lithiation of N,N-diisopropyl-2-methyl-3-phenylpropanamide (4). The beta-lithiation of 4 is highly diastereoselective with the beta-proton that is in the same relative position as the beta-proton of diastereomer 6 being preferentially removed. The beta-lithio species derived from 4 is shown to be a pyramidal, organolithium reagent based on C-13 NMR. Lithiation of the R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-(phenylthio)butanamide (7, 8) and N,N-diisopropyl-2,3-dimethyl-4-pentenamide (9, 10) occur at the beta-position. Lithiation of the R*,S* and R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-phenylbutanamide (11, 12) occurs at the beta-position for 11 and at the alpha-position for 12. A conformational model is shown to correlate with these observations. The beta-lithio species formed do not react diastereospecifically.

  DOI：

  10.1021/jo00016a025
• 作为产物：
  描述：

  N,N-diisopropyl-2-methyl-3-phenylpropanamide 在 sodium periodate 、 仲丁基锂 作用下， 生成 (Z)-N,N-Diisopropyl-2-methyl-3-phenylpropenamide
  参考文献：
  名称：

  Complex induced proximity effects: .beta.-lithiations of carboxamides

  摘要：

  The R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2,3-dideuterio-2-methyl-3-phenylpropanamide (5,6) have been used to investigate the diastereoselectivity of the beta-lithiation of N,N-diisopropyl-2-methyl-3-phenylpropanamide (4). The beta-lithiation of 4 is highly diastereoselective with the beta-proton that is in the same relative position as the beta-proton of diastereomer 6 being preferentially removed. The beta-lithio species derived from 4 is shown to be a pyramidal, organolithium reagent based on C-13 NMR. Lithiation of the R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-(phenylthio)butanamide (7, 8) and N,N-diisopropyl-2,3-dimethyl-4-pentenamide (9, 10) occur at the beta-position. Lithiation of the R*,S* and R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-phenylbutanamide (11, 12) occurs at the beta-position for 11 and at the alpha-position for 12. A conformational model is shown to correlate with these observations. The beta-lithio species formed do not react diastereospecifically.

  DOI：

  10.1021/jo00016a025

文献信息

• Iridium(<scp>iii</scp>)-catalyzed regioselective direct arylation of sp² C–H bonds with diaryliodonium salts
  作者：Pan Gao、Li Liu、Zhuangzhi Shi、Yu Yuan

  DOI：10.1039/c6ob01145d

  日期：——

  A regioselective direct arylation of arenes and olefins at the ortho position is reported. The key to the high selectivity is the appropriate choice of diaryliodonium salts as the arylating reagent in the presence of a cationic iridium(III) catalyst. The coordination of the metal with an oxygen atom or a nitrogen atom and subsequent C–H activation allows for direct arylation with coupling partners

  据报道在邻位的芳烃和烯烃的区域选择性直接芳基化。到高选择性的关键是二芳基碘盐作为阳离子铱（存在下芳基化试剂的合适的选择III）催化剂。金属与氧原子或氮原子的配位以及随后的C–H活化可实现与偶联配偶体的直接芳基化。该反应在温和的反应条件下进行，并且对包括许多卤化物官能团在内的各种官能团具有较高的耐受性。
• Photoisomerization of Alkenes via Energy Transfer Enabled by Cu‐Acetylide Complexes
  作者：Ryo Murakami、Noritaka Kojima、Ryoya Kamo、Hiroto Tanishima、Fuyuhiko Inagaki

  DOI：10.1002/ejoc.202300948

  日期：2023.12.19

  visible photosensitizers for energy transfer to alkenes. On this basis, the E→Z photoisomerization reactions of alkenes with various functional groups under blue light irradiation were performed with moderate to high selectivity. The mechanistic studies suggested that the reactions involved energy transfer (EnT) from the photo-excited copper acetylide to the alkene via the singlet excited state.

  人们发现乙炔铜配合物可作为可见光敏剂，将能量转移至烯烃。在此基础上，在蓝光照射下进行了具有不同官能团的烯烃的E→Z光异构化反应，具有中等到高选择性。机理研究表明，该反应涉及从光激发乙炔铜通过单重激发态到烯烃的能量转移（EnT）。
• Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide
  作者：José M. Concellón、Juan A. Pérez-Andrés、Humberto Rodríguez-Solla

  DOI：10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f

  日期：2001.7.16

  Stereoselective beta -elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta -unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds a are easily prepared by reaction of the corresponding lithium enolates of alpha -chloroamides with aldehydes or ketones at -78 degreesC. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta -elimination reaction is also discussed.