(2E)-3-(4-methoxyphenyl)-N,N-dimethylpropanamide | 21469-81-8

• 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: (2E)-3-(4-methoxyphenyl)-N,N-dimethylpropanamide
• 英文别名: (E)-3-(4-methoxyphenyl)-N,N-dimethylacrylamide；(E)-N,N-dimethyl-3-(4-methoxyphenyl)prop-2-enamide；(E)-N,N-dimethyl-3-(4-methoxyphenyl)acrylamide；4-Methoxy-N,-N-dimethyl-zimtsaeureamid；(E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide
• CAS: 21469-81-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: XFGAKPSPVBVUQL-RMKNXTFCSA-N

物化性质

• 熔点：
  90-95 °C
• 沸点：
  388.5±25.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-methoxyphenyl)-N,N-dimethylpropanamide 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-methoxyphenyl)-N,N-dimethylacrylamide
  参考文献：
  名称：

  锰 (I) 催化的 α,β-不饱和羰基衍生物的不对称氢化

  摘要：

  在这里，我们报告了使用手性 Mn(I) 络合物作为催化剂的 α,β-不饱和羰基衍生物的催化不对称氢膦化反应。通过 H-P 键激活，可以通过各种基于酮、酯和甲酰胺的迈克尔受体的氢膦化反应获得各种含膦的手性产物。

  DOI：

  10.1021/acs.orglett.2c04256
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-N,N-dimethylacrylamide 以 二氯甲烷 为溶剂， 生成 (2E)-3-(4-methoxyphenyl)-N,N-dimethylpropanamide
  参考文献：
  名称：

  Lewis-acid catalysis of photochemical reactions. 9. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes

  摘要：

  The spectroscopic properties and photoisomerization reactions of several (E)- and (Z)-cinnamamides have been investigated in the absence and presence of the strong Lewis acid BF3. The (E)-cinnamamides are essentially planar and exist predominantly in the enone s-cis conformation, except in the case of the alpha-methyl tertiary amide which adopts the s-trans conformation in order to minimize nonbonded repulsion. The (Z)-cinnamamides exist predominantly in the highly nonplanar s-trans conformation. This unusual conformational preference is attributed to intramolecular charge transfer from the aromatic to amide functionality. Photoisomerization efficiencies are dependent upon N-alkylation, aromatic substitution, alpha-alkylation, solvent, and excitation wavelength. These effects are attributed to the existence of two lowest energy pi,pi* singlet states (one reactive and one nonreactive) whose relative energies are dependent upon substitution. The cinnamamides from 1:1 complexes with BF3 with equilibrium constants > 10(3). Complexation alters both the electronic structure and photochemical behavior of the cinnamamides. Quantitative E --> Z isomerization has been observed for the BF3 complexes of two tertiary amides.

  DOI：

  10.1021/jo00002a015

文献信息

• Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes
  作者：Wenqing Yu、Long Liu、Tianzeng Huang、Xiangbing Zhou、Tieqiao Chen

  DOI：10.1021/acs.orglett.0c02462

  日期：2020.9.18

  decarbonylative alkenylation of aromatic carboxylic acids was developed. Under the reaction conditions, various benzoic acids including those bearing functional groups coupled to terminal alkenes, producing the corresponding internal alkenes in good to high yields. Cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat were also applicable to this

  开发了钯催化的芳族羧酸的脱羰链烯基化反应。在反应条件下，包括带有官能团的那些苯甲酸在内的各种苯甲酸与末端烯烃偶联，以高至高收率生产相应的内部烯烃。肉桂酸和生物活性苯甲酸，例如3-甲基黄酮-8-羧酸，丙磺舒，阿达帕林和非布索坦也适用于该反应，证明了该新反应在有机合成中的潜在合成价值。
• Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides
  作者：Tianlong Yang、Maojian Lu、Zhaowei Lin、Mingqiang Huang、Shunyou Cai

  DOI：10.1039/c8ob02938e

  日期：——

  Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction

  仅使用氧气作为末端氧化剂，即可开发出苄醇与N，N-二烷基乙酰胺的氧化交叉偶联反应，从而有效地为构造具有KOH，有机光催化剂曙红Y和HOH协同作用的多功能肉桂酸酯提供了新颖的新方案。在室温下可见光照射。广泛的底物范围和温和的反应条件是该转化的突出特征。
• Oxygen and Base-Free Oxidative Heck Reactions of Arylboronic Acids with Olefins
  作者：Jiwu Ruan、Xinming Li、Ourida Saidi、Jianliang Xiao

  DOI：10.1021/ja0782955

  日期：2008.2.1

  protocol for palladium-catalyzed oxidative Heck reactions of arylboronic acids with both electron-rich and -deficient olefins is described. In contrast to the normal oxidative Heck coupling, this new method works in the absence of a base, oxygen, or other external oxidants. With a wide variety of substrates tolerated, the method broadens the scope of palladium-catalyzed coupling reactions.

  描述了一种温和有效的协议，用于钯催化的芳基硼酸与富电子和缺电子烯烃的氧化 Heck 反应。与正常的氧化 Heck 耦合相反，这种新方法在没有碱、氧气或其他外部氧化剂的情况下起作用。由于可耐受多种底物，该方法拓宽了钯催化偶联反应的范围。
• Catalysis with palladium colloids supported in poly(acrylic acid)-grafted polyethylene and polystyrene
  作者：David E Bergbreiter、Andrew Kippenberger、Zhenqi Zhong

  DOI：10.1139/v06-076

  日期：2006.10.1

  Grafts of poly(acrylic acid) on polyethylene powder (PE-g-PAA) or polystyrene (PS-g-PAA) can be used to support Pd(0) crystallites that function like a homogeneous Pd(0) catalyst in some reactions. These Pd–PE-g-PAA catalysts were active in allylic substitution reactions in the presence of added phosphine ligand. A catalyst analogous to the Pd–PE-g-PAA powder catalyst on polystyrene (Pd–PS-g-PAA) was similarly active for allylic substitution and could also be used in Heck reactions at 80–100 °C in N,N-dimethylacetamide (DMA). Analysis of the product solutions for Pd leachate and a correlation of the Pd leaching with product formation in the allylic substitution chemistry for both types of catalysts suggests that the active catalysts in these reactions are leached from the support. In the case of the allylic substitution reaction, external triphenylphosphine and substrate together are required for the chemistry and Pd leaching.Key words: catalysis, palladium, allylic substitution, grafted polystyrene, supported catalysts.

  在聚乙烯粉末（PE-g-PAA）或聚苯乙烯（PS-g-PAA）上接枝聚（丙烯酸）可用于支撑钯（0）结晶，在某些反应中可发挥均相钯（0）催化剂的作用。在添加膦配体的情况下，这些 Pd-PE-g-PAA 催化剂在烯丙基取代反应中具有活性。与聚苯乙烯上的 Pd-PE-g-PAA 粉末催化剂类似的催化剂（Pd-PS-g-PAA）在烯丙基取代反应中也具有类似的活性，并可在 80-100 °C 的 N,N-二甲基乙酰胺（DMA）中用于赫克反应。对产品溶液中的钯浸出物进行分析，以及钯浸出物与两种催化剂在烯丙基取代化学反应中生成的产品之间的相关性表明，这些反应中的活性催化剂是从载体中浸出的。在烯丙基取代反应中，化学反应和钯浸出需要外部三苯基膦和底物的共同作用。
• Rhodium-Catalyzed Heck-Type Coupling of Boronic Acids with Activated Alkenes in an Aqueous Emulsion
  作者：Mark Lautens、John Mancuso、Harpreet Grover

  DOI：10.1055/s-2004-829161

  日期：——

  Intermolecular couplings between arylboronic acids and activated alkenes catalyzed by a water-soluble tert-butyl amphosrhodium complex were found to progress at room temperature and generated Heck-type products with high yields and excellent selectivity. Substitution on the alkene component encouraged the formation of products arising from a conjugate addition-protonation process. In the case of Heck

  发现由水溶性叔丁基氨磷络合物催化的芳基硼酸和活化烯烃之间的分子间偶联在室温下进行，并以高产率和优异的选择性生成 Heck 型产物。烯烃组分上的取代促进了由共轭加成质子化过程产生的产物的形成。在 Heck 产物形成的情况下，必须添加两当量的烯烃组分，据信其中一当量用作牺牲氢化物受体。