N-allyl-N-(4-methoxyphenyl)-acetamide | 119561-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-allyl-N-(4-methoxyphenyl)-acetamide
• 英文别名: N-allyl-N-(4-methoxyphenyl)acetamide；N-allyl-4-methoxyacetanilide；Acetamide, N-(4-methoxyphenyl)-N-2-propenyl-；N-(4-methoxyphenyl)-N-prop-2-enylacetamide
• CAS: 119561-01-2
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: YEKQOZBZTXLIHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-allyl-N-(4-methoxyphenyl)-acetamide 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 生成 (E)-ethyl 5-(N-(4-methoxyphenyl)acetamido)-4-((ethoxycarbonothioyl)thio)pent-2-enoate
  参考文献：
  名称：

  A Convenient Conversion of Terminal Alkenes into Homologous Unsaturated and Doubly Unsaturated Esters

  摘要：

  Unsaturated and doubly unsaturated esters have been synthesized in two steps by the application of a radical xanthate transfer process of a simple methylsulfoxide starting material to a range of terminal alkenes. syn-Elimination of the sulfoxide gives alpha,beta-unsaturated esters, which coupled with a xanthate elimination yields alpha,beta,gamma,delta-unsaturated esters.

  DOI：

  10.1021/ol203387r
• 作为产物：
  描述：

  甲氧苯胺 在 Ni{α,α'-bis(diphenylphosphino)-o-xylene}2 、 sodium acetate 、 溶剂黄146 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 生成 N-allyl-N-(4-methoxyphenyl)-acetamide
  参考文献：
  名称：

  镍(0)-催化酰胺和对甲苯磺酰胺与烯丙醇在纯净和中性条件下的N-烯丙基化

  摘要：

  镍（0）催化酰胺和对甲苯磺酰胺与烯丙醇的直接 N-烯丙基化发生在 Ni0-二膦配合物的存在下。在中性条件下以中等至高产率获得相应的 N-烯丙基化（和/或 N,N-二烯丙基化）产物。

  DOI：

  10.1002/ejoc.201600500

文献信息

• A Practical Ruthenium-Catalyzed Cleavage of the Allyl Protecting Group in Amides, Lactams, Imides, and Congeners
  作者：Benito Alcaide、Pedro Almendros、Jose M. Alonso

  DOI：10.1002/chem.200501227

  日期：2006.3.20

  deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl(3) (oxidation step). A variety of substrates, including enantiopure multifunctional beta- and gamma-lactams, can

  开发了一种方便的方法，用于脱保护N-烯丙基酰胺样部分。通过顺序使用Grubbs卡宾（异构化步骤）和RuCl（3）（氧化步骤）获得了第一个实例，说明了钌催化的酰胺，内酰胺，酰亚胺，吡唑烷酮，乙内酰脲和恶唑烷酮的脱羧反应。可以使用多种底物，包括对映纯多功能β-和γ-内酰胺。
• A Next‐Generation Air‐Stable Palladium(I) Dimer Enables Olefin Migration and Selective C−C Coupling in Air
  作者：Gourab Kundu、Theresa Sperger、Kari Rissanen、Franziska Schoenebeck

  DOI：10.1002/anie.202009115

  日期：2020.12

  We report a new air‐stable PdI dimer, [Pd(μ‐I)(PCy2tBu)]2, which triggers E‐selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C−C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C−Br, C−OTf/OFs, and

  我们报告了一种新的空气稳定的Pd I二聚体[Pd（μI）（PCy 2 t Bu）] 2，它在存在多个官能团且具有完全耐受性的情况下触发E-选择性烯烃向酰胺和苯乙烯衍生物的迁移空气 同一二聚体还可以在室温下以模块化和三重选择性的方式在聚（假）卤代芳烃中以芳族C-Br，C-OTf / OF和C-Cl键的形式快速触发C-C偶联（烷基化和芳基化）在具有邻位C-OTf的取代基的底物上显示出比以前的Pd I二聚体更好的活性。
• Highly selective synthesis of (E)-N-aryl-N-(1-propenyl) ethanamides via isomerization of N-allyl ethanamides catalyzed by ruthenium complexes
  作者：Stanislaw Krompiec、Mariola Pigulla、Wojciech Szczepankiewicz、Tadeusz Bieg、Nikodem Kuznik、Katarzyna Leszczynska-Sejda、Maciej Kubicki、Teresa Borowiak

  DOI：10.1016/s0040-4039(01)01457-5

  日期：2001.10

  A convenient and highly selective method of synthesis of (E)-N-aryl-N-(1-propenyl)ethanamides via isomerization of respective N-allyl-N-arylethanamides catalyzed by [RuClH(CO)(PPh3)(3)] has been described. N-Allyl-N-arylethanamides have been obtained by allylation of respective N-arylethanamides under PTC conditions. It is proposed that the observed selectivity of the double bond migration to (E)-enamides is due to the interaction of the arene ring with the Ru atom in the transition state. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Lebedev, S. A.; Leonova, Yu. P.; Berestova, S. S., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 5, p. 1005 - 1006
  作者：Lebedev, S. A.、Leonova, Yu. P.、Berestova, S. S.、Petrov, E. S.

  DOI：——

  日期：——
• LEBEDEV, S. A.;LEONOVA, YU. P.;BERESTOVA, S. S.;PETROV, EH. S., ZH. ORGAN. XIMII, 24,(1988) N 5, 1112-1113
  作者：LEBEDEV, S. A.、LEONOVA, YU. P.、BERESTOVA, S. S.、PETROV, EH. S.

  DOI：——

  日期：——