2-丙烯酰胺,N,N-二甲基-3-苯基-,(2E)- | 17431-39-9

• 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
• 中文名称: 2-丙烯酰胺,N,N-二甲基-3-苯基-,(2E)-
• 英文名称: (E)-N,N-dimethylcinnamamide
• 英文别名: N,N-dimethylcinnamamide；(E)-N,N-dimethyl-3-phenylprop-2-enamide；trans-N,N-dimethylcinnamamide；N,N-dimethylcinnamide
• CAS: 17431-39-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: AGTDAKUUKGHNCK-CMDGGOBGSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  335.1±21.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-丙烯酰胺,N,N-二甲基-3-苯基-,(2E)- 在 叔丁基过氧化氢 三苯胂氧化物 、 S-1,1'-联-2-萘酚 、 samarium(III) isopropoxide 作用下， 以 四氢呋喃 、 癸烷 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+
• 作为产物：
  描述：

  肉桂酰胺 在 水 、 氢碘酸 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 2-丙烯酰胺,N,N-二甲基-3-苯基-,(2E)-
  参考文献：
  名称：

  碘化氢对 α,β-不饱和羰基和羧基化合物的化学选择性还原

  摘要：

  用 HI 水溶液选择性还原 α,β-不饱和羰基化合物以制备饱和羰基化合物。在α或β位引入芳基是有效的...

  DOI：

  10.1246/bcsj.20200341

文献信息

• Copper catalyzed cross-coupling reactions of carboxylic acids: an expedient route to amides, 5-substituted γ-lactams and α-acyloxy esters
  作者：S. Priyadarshini、P. J. Amal Joseph、M. Lakshmi Kantam

  DOI：10.1039/c3ra41000e

  日期：——

  A convenient and recyclable catalytic protocol for the synthesis of N,N-dimethyl substituted amides, 5-substituted γ-lactams and α-acyloxy ethers from carboxylic acids using CuO nanoparticles and TBHP is described.

  描述了使用CuO纳米颗粒和TBHP从羧酸合成N，N-二甲基取代的酰胺，5-取代的γ-内酰胺和α-酰氧基醚的方便且可回收的催化方案。
• 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。
• General and Mild Cobalt-Catalyzed C-Alkylation of Unactivated Amides and Esters with Alcohols
  作者：Nicklas Deibl、Rhett Kempe

  DOI：10.1021/jacs.6b06448

  日期：2016.8.31

  The borrowing hydrogen or hydrogen autotransfer methodology is an elegant and sustainable or green concept to construct carbon-carbon bonds. In this concept, alcohols, which can be obtained from barely used and indigestible biomass, such as lignocellulose, are employed as alkylating reagents. An especially challenging alkylation is that of unactivated esters and amides. Only noble metal catalysts based

  借用氢或氢自动转移方法是构建碳-碳键的优雅且可持续或绿色的概念。在这个概念中，可以从几乎不使用且难以消化的生物质（例如木质纤维素）中获得的醇被用作烷基化试剂。一个特别具有挑战性的烷基化是未活化的酯和酰胺。仅使用基于铱和钌的贵金属催化剂来完成这些反应。在此，我们报告了醇对未活化酰胺和酯的第一个贱金属催化的 α-烷基化反应。我们实验室最近开发的钳形配体稳定的钴配合物可以非常有效地催化这些反应。预催化剂可以很容易地从市售的起始材料以多克规模合成，并且在碱性反应条件下自活化。这种 Co 催化剂类别还能够介导酯和酰胺的烷基化反应。此外，我们应用该方法合成酮并将醇转化为由两个碳原子拉长的醛。
• Cu(<scp>ii</scp>)-Mediated keto C(sp³)–H bond α-acyloxylation of N,N-dialkylamides with aromatic carboxylic acids
  作者：Wenjing Li、Changzhen Yin、Xiao Yang、Hailong Liu、Xueli Zheng、Maolin Yuan、Ruixiang Li、Haiyan Fu、Hua Chen

  DOI：10.1039/c7ob01190c

  日期：——

  The first example of Cu(ii)-mediated oxidative coupling of aromatic carboxylic acids with the C(sp³)–H bond adjacent to the keto group ofN,N-dialkylamides has been developed.

  铜(II)催化的芳香羧酸与N,N-二烷基酰胺的酮基邻位C(sp³)–H键的氧化偶联的第一个例子已经被开发出来。

• An Efficient and General Method for the Heck and Buchwald–Hartwig Coupling Reactions of Aryl Chlorides
  作者：Dong-Hwan Lee、Abu Taher、Shahin Hossain、Myung-Jong Jin

  DOI：10.1021/ol202177k

  日期：2011.10.21

  The β-diketiminatophosphane Pd complex acted as a powerful catalyst for the Heck coupling of aryl chlorides with alkenes. Various aryl and heteroaryl chlorides were coupled efficiently under relatively mild conditions. Furthermore, this catalytic system also proved to be highly active in the Buchwald–Hartwig coupling of deactivated and sterically hindered aryl chlorides at room temperature.

  β-二酮基亚氨基膦Pd络合物可作为芳基氯化物与烯烃的Heck偶联的有力催化剂。在相对温和的条件下有效地偶联了各种芳基和杂芳基氯化物。此外，在室温下，这种催化体系在失活的和位阻的芳基氯化物的布赫瓦尔德-哈特维格偶联中也被证明具有很高的活性。