N-allyl-N-(4-bromo-phenyl)acetamide | 119561-02-3

• 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-(4-bromo-phenyl)acetamide
• 英文别名: Acetamide, N-(4-bromophenyl)-N-2-propenyl-；N-(4-bromophenyl)-N-prop-2-enylacetamide
• CAS: 119561-02-3
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: LWYUYECOWXDCPG-UHFFFAOYSA-N

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-(4-bromo-phenyl)acetamide 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 4.0h， 生成 dithiocarbonic acid [4-(1-acetyl-5-bromo-2,3-dihydro-1H-indol-3-yl)-2-oxo-butyl] ester ethyl ester
  参考文献：
  名称：

  S-(3-Chloro-2-oxo-propyl)-O-ethyl xanthate: a linchpin radical coupling agent for the synthesis of heterocyclic and polycyclic compounds

  摘要：

  本文描述了S-(3-氯-2-氧代丙基)-O-乙基黄原酸酯的制备与使用，该化合物可直接引入α-氯酮基团，并应用于合成杂环和多环结构。

  DOI：

  10.1039/b514509k
• 作为产物：
  描述：

  4'-溴乙酰苯胺 、 3-溴丙烯 在 sodium hydroxide 作用下， 生成 N-allyl-N-(4-bromo-phenyl)acetamide
  参考文献：
  名称：

  S-(3-Chloro-2-oxo-propyl)-O-ethyl xanthate: a linchpin radical coupling agent for the synthesis of heterocyclic and polycyclic compounds

  摘要：

  本文描述了S-(3-氯-2-氧代丙基)-O-乙基黄原酸酯的制备与使用，该化合物可直接引入α-氯酮基团，并应用于合成杂环和多环结构。

  DOI：

  10.1039/b514509k

文献信息

• Synthesis of cyanoalkyl indolines through cyanoalkylarylation of N-allyl anilines with alkyl nitriles under metal-free and neutral conditions
  作者：Deqiang Liang、Xuemei Song、Lichun Xu、Yitong Sun、Ying Dong、Baoling Wang、Weili Li

  DOI：10.1016/j.tet.2019.05.018

  日期：2019.6

  An α-C(sp3)−H functionalization of alkyl nitriles under metal-free and neutral conditions is presented. In the presence of di-tert-butyl peroxide (DTBP), N-allyl anilines underwent exo-selective cyanoalkylation/cyclization cascade, providing a direct access to 3-cyanoalkyl indolines. Previously, a transition-metal catalyst and/or a strong base were generally required to activate nitrilic α-C−H bonds

  提出了在无金属和中性条件下烷基腈的α-C（sp 3）-H官能化。在二-的存在下叔丁基过氧化物（DTBP），ñ -烯丙基苯胺后行外型-选择性氰烷基化/环化级联，提供到3-氰基二氢吲哚的直接访问。以前，通常需要过渡金属催化剂和/或强碱来激活腈基α-CH键。该反应具有广泛的底物范围和低成本，并且伯，仲和叔吲哚-3-基腈都可以组装。
• Iron-Catalyzed <i>exo</i> -Selective Synthesis of Cyanoalkyl Indolines via Cyanoisopropylarylation of Unactivated Alkenes
  作者：Yanni Li、Yu Chang、Yufen Li、Cheng Cao、Jinshuang Yang、Baoling Wang、Deqiang Liang

  DOI：10.1002/adsc.201800296

  日期：2018.7.4

  An iron‐catalyzed cyanoalkylation using azobisisobutyronitrile (AIBN) is reported. With unactivated double bond as the radical acceptor, N‐allyl anilines underwent cyanoisopropylation/cyclization cascade to afford 3‐cyanoalkyl indolines bearing a tertiary nitrile moiety, which were otherwise unavailable. Excellent exo‐selectivity was always observed, and such a selectivity and the unusual performance

  据报道，使用偶氮二异丁腈（AIBN）的铁催化氰基烷基化反应。N-烯丙基苯胺以未活化的双键为自由基受体，进行氰基异丙基化/环化级联反应，生成带有叔腈部分的3-氰基烷基二氢吲哚，否则无法得到。始终观察到极好的外向选择性，铁催化剂的这种选择性和异常的性能可能与自由基和底物之间的金属桥联有关。
• Synthesis of 2,3-Dihydrotryptamines from Amide Solvents and Acyclic Materials through Metal-Free Amidoalkylarylation of Unactivated Alkenes
  作者：Yubin Ji、Siping Yang、Shiyi Lin、Yan Wang、Chenfeng Ji、Yingjie Liu、Deqiang Liang

  DOI：10.1055/s-0037-1611825

  日期：2019.7

  The first synthesis of 2,3-dihydrotryptamines from acyclic materials and an exo-selective amidoalkylation/cyclization cascade of N-allyl anilines through α-C(sp3)–H functionalization of simple amides across unactivated alkenes are presented. This reaction proceeds in mixed aqueous media and under metal-free conditions and features a broad substrate scope and a simple operation.

  首次从无环材料合成 2,3-二氢色胺和 N-烯丙基苯胺的外选择性酰胺烷基化/环化级联，通过 α-C(sp3)-H 对未活化烯烃的简单酰胺进行官能化。该反应在混合水介质和无金属条件下进行，具有底物范围广、操作简单等特点。
• Radical Arylaminomethylation of Unactivated Alkenes
  作者：Frédéric Lebreux、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol901055j

  日期：2009.7.2

  Xanthates derived from open chain or cyclic N-chloromethylanilides are capable of adding to various unactivated alkenes to give adducts which, in suitable cases, can be made to undergo ring closure onto the aromatic ring. This flexible arylaminomethylation of alkenes allows the rapid synthesis of open chain or polycyclic aniline derivatives.
• 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.

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