N-烯丙基-2-溴乙酰胺 | 126265-30-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-烯丙基-2-溴乙酰胺
• 英文名称: N-allyl-2-bromoacetamide
• 英文别名: 2-Bromo-N-(prop-2-EN-1-YL)acetamide；2-bromo-N-prop-2-enylacetamide
• CAS: 126265-30-3
• 化学式: C₅H₈BrNO
• mdl: MFCD06799645
• 分子量: 178.029
• InChiKey: DIURKPUKYORPET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-烯丙基-2-溴乙酰胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 2,6-二叔丁基-4-甲基苯酚 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (Z)-1,9-Dioxa-4-aza-cycloheptadec-6-en-3-one
  参考文献：
  名称：

  Using Cross-Metathesis to Couple l-Phenylalanine to a Macrocyclic Lactam

  摘要：

  Grubbs' second generation ruthenium catalyst was used to Couple the amino acid L-phenylalanine to a 17-membered lactam, using cross-metathesis with an E-alkene favored in the process. The best coupling conditions have the product in 48% yield. The reversibility of the process was also confirmed. Ring-closing metathesis was a key reaction used to form the macrocyclic lactam.

  DOI：

  10.1021/jo052415e
• 作为产物：
  描述：

  溴乙酰氯 、 丙烯胺 在 乙醚 作用下， 生成 N-烯丙基-2-溴乙酰胺
  参考文献：
  名称：

  Bergmann; Dreyer; Radt, Chemische Berichte, 1921, vol. 54, p. 2148

  摘要：

  DOI：

文献信息

• Selective Synthesis of Isoquinolin-3-one Derivatives Combining Pd-Catalysed Aromatic Alkylation/Vinylation with Addition Reactions: The Beneficial Effect of Water
  作者：Raffaella Ferraccioli、Alessandra Forni

  DOI：10.1002/ejoc.200900255

  日期：2009.7

  The three-component, palladium/norbornene-catalysed reaction of 1, haloamides 2 and properly substituted olefins 3 performed in DMF/water at 80 °C selectively gave 5 and 6 through three- and four-bond-forming reactions, respectively. The presence of water was crucial to obtain products in fair to good yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  1、卤代酰胺 2 和适当取代的烯烃 3 在 DMF/水中在 80°C 下进行的三组分钯/降冰片烯催化反应分别通过三键和四键形成反应选择性地得到 5 和 6。水的存在对于以一般到良好的收率获得产品至关重要。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Combining α-amidoalkylation reactions of N-acyliminium ions with ring-closing metathesis: access to versatile novel isoindolones spirocyclic compounds
  作者：Anthony Pesquet、Mohamed Othman

  DOI：10.1016/j.tetlet.2013.07.077

  日期：2013.9

  A novel approach to diversely spirocyclic isoindoles has been developed by using N-acyliminium/ring-closing metathesis strategy. Spirocyclization precursors, diolefinic, and enyne spiro-fused-isoindole derivatives have been obtained by a regioselective reduction of the spiro-imide compounds, followed by the allylation of the N-acyliminium intermediates (generated from the acetoxylactam compounds).

  通过使用N-酰基亚胺/环闭合复分解策略，已经开发了一种新颖的方法用于不同的螺环异吲哚。螺环化前体，二烯烃和烯炔螺-稠合-异吲哚衍生物是通过将螺-酰亚胺化合物进行区域选择性还原，然后将N-酰基酰亚胺中间体（由乙酰氧基内酰胺化合物生成）烯丙基化而获得的。上述不饱和衍生物的钌催化的闭环复分解反应提供了新的螺异吲哚。
• Aza-heterocyclic frameworks through intramolecular π-system trapping of spiro-<i>N</i>-acyliminiums generated from isoindolinone
  作者：Sarra Chortani、Mohamed Othman、Ata Martin Lawson、Anis Romdhane、Hichem Ben Jannet、Michael Knorr、Lukas Brieger、Carsten Strohmann、Adam Daïch

  DOI：10.1039/d0nj04052e

  日期：——

  spiro-isoindolinone-imides. The latter were produced in large scale in three steps from homophthalic acid. These imides were useful to provide in one step isoindolinones bearing hydroxymethyl-amide functions, tethered at quaternary carbon centre with promising biological issues. Submitted to Brønsted (TFA neat) and Lewis acid (trimethylsilyltrifluoro-methanesulfonic (TMSOTf) 10 mol%), the spiro-acetoxylactams undergo

  通过螺-异吲哚满酮-酰亚胺的串联区域选择性还原/ O-酰化反应直接获得了作为主要底物的螺-乙酰氧基内酰胺。后者是由间苯二甲酸分三步大规模生产的。这些酰亚胺可用于一步提供具有羟甲基酰胺官能团的异吲哚啉酮，该化合物被季铵碳中心束缚，并具有潜在的生物学问题。螺-乙酰氧基内酰胺经Brønsted（TFA纯净）和路易斯酸（三甲基甲硅烷基三氟甲磺酸（TMSOTf）10摩尔％）进行π-环化N-酰基亚胺，非对映选择性地提供与芳族体系稠合或不稠合的π-芳族原始吡咯并吡咯并吡咯并氮杂庚烯-异吲哚。用π-烯烃，分离出与异吲哚啉融合或含有氨基酸的吡咯并吡啶和吡咯并-氮杂。还讨论了产生所有这些系统的反应机理。
• Formal [3+2]-Cycloaddition-Based Approach Using Ethoxymethylene Malonate Derivatives: Novel and Expedient Access to Functionalized N-Acyliminium Precursors
  作者：Sébastien Comesse、Vincent Dalla、Adam Daïch、Moussa Saber、Morgane Sanselme、Pierre Netchitaïlo

  DOI：10.1055/s-0030-1258530

  日期：2010.9

  Combination of a base, ethoxymethylene malonates, and α-bromoacetamides was used to reach structurally diverse α-alkoxy-γ-lactams via a direct aza-MIRC sequence in excellent yields. Subsequent acidic treatment allowed the formed pyrrolo [2,1-a]isoquinoline alkaloid core to be isolated in high yield.

  利用碱、乙氧基亚甲基丙二酸盐和δ±-溴乙酰胺的组合，通过直接偶氮-MIRC 顺序制备出结构多样的δ±-烷氧基δ³-内酰胺，收率极高。随后的酸性处理使形成的吡咯并[2,1-a]异喹啉生物碱核心得以高产分离。
• Ruthenium(<scp>ii</scp>)-catalyzed C–H activation and (4+2) annulation of aromatic hydroxamic acid esters with allylic amides
  作者：Chandan Kumar Giri、Suman Dana、Mahiuddin Baidya

  DOI：10.1039/d1cc04422b

  日期：——

  using aromatic hydroxamic acid esters as the oxidizing directing group and allylic amides as unactivated olefin coupling partners, delivering a wide variety of aminomethyl isoquinolinones in good to excellent yields. This annulation is distinctive as allylic congeners typically result in allylation and not the annulation. Late-stage derivatization of a bioactive synthetic bile acid has been showcased

  据报道，在 Ru( II ) 催化下的 (4+2) 环化使用芳族异羟肟酸酯作为氧化导向基团，烯丙基酰胺作为未活化的烯烃偶联伙伴，以良好到优异的产率提供各种氨甲基异喹啉酮。这种环化是独特的，因为烯丙基同类物通常导致烯丙基化而不是环化。已经展示了生物活性合成胆汁酸的后期衍生化。