3-(4-methoxyphenyl)-N,N-dimethylacrylamide | 131214-24-9

• 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: 3-(4-methoxyphenyl)-N,N-dimethylacrylamide
• 英文别名: (Z)-3-(4-methoxyphenyl)-N,N-dimethylacrylamide；(Z)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide
• CAS: 131214-24-9
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: XFGAKPSPVBVUQL-TWGQIWQCSA-N

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：

  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
• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 在 4-二甲氨基吡啶 、 1,1'-双(二苯基膦)二茂铁 、 甲基二乙氧基硅烷 、 lithium methanolate 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(4-methoxyphenyl)-N,N-dimethylacrylamide
  参考文献：
  名称：

  CuCl 2催化高度立体选择性和化学选择性将炔基酰胺还原为α，β-不饱和酰胺，使用硅烷作为氢供体

  摘要：

  利用硅烷作为氢供体，开发了CuH催化的炔基酰胺的Z选择性部分还原，制得α，β-不饱和酰胺。该反应在温和的条件下进行，能够容纳广泛的炔基酰胺，包括带有末端碳-碳双键或三键的炔基酰胺，从而提供具有高立体选择性和优异收率的烯基酰胺。

  DOI：

  10.1039/d0ob02037k

文献信息

• 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。
• Rationally Designed Pincer-Type Heck Catalysts Bearing Aminophosphine Substituents: Pd^IVIntermediates and Palladium Nanoparticles
  作者：Jeanne L. Bolliger、Olivier Blacque、Christian M. Frech

  DOI：10.1002/chem.200800441

  日期：2008.9.8

  catalytic cycle of the Heck reaction, their general existence as reactive intermediates (for example, in other reactions) cannot be excluded. On the contrary, they were shown to be thermally accessible. Compounds 1 and 2 show a smooth halide exchange with bromobenzene to yield their bromo derivatives in DMF at 100 degrees C. Experimental observations revealed that the halide exchange most probably proceeded

  氨基膦基钳形配合物[C6H3-2,6-（XP（哌啶基）2）2Pd（Cl）]（X = NH 1; X = O 2）可以很容易地由廉价的起始原料通过依次添加1,1在“一锅”中，在N 2下，将'，1''-膦三基三哌啶和1,3-二氨基苯或间苯二酚制得[Pd（cod）（Cl）2]（cod =环辛二烯）在甲苯中的溶液。事实证明，化合物1和2是出色的Heck催化剂，可以在很短的反应时间和较低的催化剂负载量下，在140℃下将数种电子失活和空间位阻的芳基溴化物与各种烯烃作为偶联伴侣进行定量偶联。升高的反应温度还使得在仅0.01mol％的催化剂存在下，烯烃能够与电子失活的和位阻的芳基氯有效地偶联。进行的机理研究排除了均相的Pd 0配合物是1和2的催化活性形式。另一方面，钯纳米颗粒参与催化循环得到了有力的实验支持。即使衍生自1（和2）的钳型Pd IV中间体不参与Heck反应的催化循环，也不能排除它们作为反应性中
• Visible-Light-Enabled Oxidative Coupling of Alkenes with Dialkylformamides To Access Unsaturated Amides
  作者：Maojian Lu、Zhaowei Lin、Shanyi Chen、Hongyou Chen、Mingqiang Huang、Shunyou Cai

  DOI：10.1021/acs.orglett.9b03870

  日期：2019.12.20

  A practical and direct method for oxidative cross-coupling of alkenes with dialkylformamides is established employing visible-light-enabled photoredox catalysis. This strategy allows efficient access to diverse unsaturated amides under mild reaction conditions. The application of an appropriate diaryliodonium salt was demonstrated to be critical to the success of this process. This catalyst system

  建立了一种实用且直接的方法，利用可见光使能的光氧化还原催化作用，将烯烃与二烷基甲酰胺进行氧化交联。该策略允许在温和的反应条件下有效地获得各种不饱和酰胺。事实证明，适当的二芳基碘鎓盐的应用对于该方法的成功至关重要。该催化剂体系对各种有用的官能团具有良好的耐受性。
• Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes
  作者：Chuan-Qi Zhao、Yue-Gang Chen、Hui Qiu、Lei Wei、Ping Fang、Tian-Sheng Mei

  DOI：10.1021/acs.orglett.9b00148

  日期：2019.3.1

  Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.

  开发了使用H 2 O作为氢源和Mn作为还原剂的钯催化炔烃转移半氢化反应，在温和条件下选择性提供了顺式和反式烯烃。此外，此方法通过使用D 2 O代替H 2 O提供了一种有效的方法来访问各种顺式-1,2-杂二烯基烯烃和反式-1,2-杂二烯基烯烃。
• Configuration-dependent photoisomerization of (E)-cinnamamides
  作者：Frederick D. Lewis、Jeffrey E. Elbert、Alana L. Upthagrove、Paul D. Hale

  DOI：10.1021/ja00223a048

  日期：1988.7

  Effets des substituants de l'azote et du cycle benzenique sur la photoisomerisation dans l'UV proche des composes ci-dessus

  Effets des substituants de l'azote et du cycle benzenique sur la photoisomerisation dans l'UV proche des composes ci-dessus