N-allyl-N-(2-chloro-phenyl)-acetamide | 207992-40-3

• 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-(2-chloro-phenyl)-acetamide
• 英文别名: N-(2-chlorophenyl)-N-prop-2-enylacetamide
• CAS: 207992-40-3
• 化学式: C₁₁H₁₂ClNO
• 分子量: 209.675
• InChiKey: JDFLKTXQNYPGCU-UHFFFAOYSA-N

物化性质

• 沸点：
  320.637±35.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.158±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 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：

  N-allyl-N-(2-chloro-phenyl)-acetamide 在 反式-1,2-二苯乙烯 、 N,N,N,N-tetraethylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 1.03h， 以67%的产率得到1-(3-methylindolin-1-yl)ethanone
  参考文献：
  名称：

  Formation of N-Acetyl-2,3-dihydroindoles by the Electrochemical Cleavage of the Carbon-Chlorine Bond in N-Allyl-2-chloroacetanilides.

  摘要：

  The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.

  DOI：

  10.3891/acta.chem.scand.52-0549
• 作为产物：
  描述：

  N-(2-chlorophenyl)-N-[(E)-3-phenylprop-2-enyl]acetamide 在 反式-1,2-二苯乙烯 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.75h， 生成 N-allyl-N-(2-chloro-phenyl)-acetamide
  参考文献：
  名称：

  Formation of N-Acetyl-2,3-dihydroindoles by the Electrochemical Cleavage of the Carbon-Chlorine Bond in N-Allyl-2-chloroacetanilides.

  摘要：

  The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.

  DOI：

  10.3891/acta.chem.scand.52-0549

文献信息

• 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.
• Syntheses of 3-Substituted 2,3-Dihydrobenzofuranes, 1,2-Dihydronaphtho(2,1-<i>b</i>)furanes, and 2,3-Dihydro-1<i>H</i>-indoles by Tandem Ring Closure−S_RN1 Reactions
  作者：Santiago E. Vaillard、Al Postigo、Roberto A. Rossi

  DOI：10.1021/jo026404m

  日期：2002.11.1

  3-Substituted 2,3-dihydrobenzofuranes (7a-c), 1,2-dihydronaphtho(2,1-b)furanes (10a-c), and N-substituted 2,3-dihydro-1H-indoles (8a-c, 9a,b) are obtained in very good yields by S(RN)1 photostimulated reactions in liquid ammonia from adequate haloaromatic compounds ortho-substituted with a suitable double bond (3a,b; 4a,b; 5a; 6a,b) and Me3Sn-, Ph2P-, and -CH2NO2 anions. The novelty of the work involves the versatile application of a 5-exo ring closure process during the propagation cycle of the SRN1 reaction; the alkyl radical intermediates formed react with the nucleophiles to afford the ring closure-substituted heterocycles. The factors governing the observed product distribution are discussed.