(Z)-N,N-dimethyl-5-phenylpent-2-enamide

• 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: (Z)-N,N-dimethyl-5-phenylpent-2-enamide
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: RVSYQBJQESNDBV-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯丙醛 、 N,N-dimethyldiazoacetamide 在 copper(l) iodide 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (Z)-N,N-dimethyl-5-phenylpent-2-enamide 、 5-phenyl-pent-2-enoic acid dimethylamide
  参考文献：
  名称：

  铜（I）催化醛缩醛化反应中的重氮试剂

  摘要：

  描述了在碘化铜（I）存在下使用重氮试剂和三苯基膦将醛烯化以合成不饱和酮，酯，酰胺和膦酸酯。对于多种脂族，芳族和杂芳族醛，均获得了良好的E：Z选择性和良好的收率。该反应还显示出优异的官能团相容性，并且在酮，硝基，胺，醚，缩醛，硫醚和卤化物基团的存在下醛被选择性地反应。与先前报道的昂贵的过渡金属络合物相比，使用成本有效的铜盐作为催化剂是有利的。该方法用于scutifoliamide A的全合成，scutifoliamide A是一种具有抗真菌活性的生物活性化合物。

  DOI：

  10.1002/adsc.200800381

文献信息

• Highly<i>Z</i>-Selective Synthesis of Disubstituted α,β-Unsaturated Cyanides and Amides Using 10-P-5 Wittig Type Reagents
  作者：Satoshi Kojima、Kazuhiro Kawaguchi、Shiro Matsukawa、Keiichiro Uchida、Kin-ya Akiba

  DOI：10.1246/cl.2002.170

  日期：2002.2

  bearing cyanomethyl, acetamide, and N,N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α,β-unsaturated cyanides with high Z-selectivity in the case of aliphatic aldehydes (Z:E=94:6 to 99:1). On the other hand, the reactions of the two amide reagents with aldehydes yielded

  检查带有氰甲基、乙酰胺和 N,N-二甲基乙酰胺基团的磷烷 (10-P-5) 的 Wittig 型反应。所有三个反应得到相应的烯烃。在脂肪醛的情况下，氰甲基试剂与醛反应得到具有高 Z-选择性的 α,β-不饱和氰化物（Z:E=94:6 至 99:1）。另一方面，两种酰胺试剂与醛的反应产生了 α,β-不饱和酰胺，对芳香族和脂肪族醛都具有高 Z 选择性（Z:E=99:1 至 >99:<1）。
• <i>Z</i>-Selective Synthesis of α,β-Unsaturated Amides with Triphenylsilylacetamides
  作者：Satoshi Kojima、Hiroki Inai、Tsugihiko Hidaka、Tomohide Fukuzaki、Katsuo Ohkata

  DOI：10.1021/jo0161936

  日期：2002.6.1

  With the purpose of developing a method of preparing Z-alpha,beta-unsaturated amides, the Peterson reaction of the (triphenylsilyl)acetamide Ph(3)SiGH(2)COX (1, X = NBn2; 3, X = NMe2) with various aldehydes was examined. The reaction of aromatic aldehydes gave selectivities up to > 97:3. It was found that the selectivity was a function of the electronic nature of the aromatic ring and higher Z selectivity was attained with electron-rich aldehydes. With aliphatic aldehydes selectivities up to 92:8 were achieved, and unlike with analogous phosphorus reagents, less sterically hindered aldehydes gave higher Z selectivity. Also, 3, which has a smaller amide group than 1, tended to give rise to higher selectivity. A comparison with the reaction of trimethylsilyl analogues revealed the significance of the phenyl substituents on the silyl group.
• Diazo Reagents in Copper(I)-Catalyzed Olefination of Aldehydes
  作者：Hélène Lebel、Michaël Davi

  DOI：10.1002/adsc.200800381

  日期：2008.10.6

  The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility

  描述了在碘化铜（I）存在下使用重氮试剂和三苯基膦将醛烯化以合成不饱和酮，酯，酰胺和膦酸酯。对于多种脂族，芳族和杂芳族醛，均获得了良好的E：Z选择性和良好的收率。该反应还显示出优异的官能团相容性，并且在酮，硝基，胺，醚，缩醛，硫醚和卤化物基团的存在下醛被选择性地反应。与先前报道的昂贵的过渡金属络合物相比，使用成本有效的铜盐作为催化剂是有利的。该方法用于scutifoliamide A的全合成，scutifoliamide A是一种具有抗真菌活性的生物活性化合物。