N-allyl-3-bromobenzamide | 35306-76-4

• 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-3-bromobenzamide
• 英文别名: Benzamide, 3-bromo-N-allyl-；3-bromo-N-prop-2-enylbenzamide
• CAS: 35306-76-4
• 化学式: C₁₀H₁₀BrNO
• mdl: MFCD00463104
• 分子量: 240.099
• InChiKey: FKQIRPAJTGEQMC-UHFFFAOYSA-N

物化性质

• 沸点：
  344.6±35.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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-allyl-3-bromobenzamide 在 叔丁基过氧化氢 、 copper(l) iodide 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以70%的产率得到2-(3-bromophenyl)-5-(iodomethyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  CuI/TBHP: A versatile reagent system for the synthesis of 5-iodomethyl-2-aryl-4,5-dihydrooxazoles from N-allylarylamides

  摘要：

  Herein, a novel reagent system using CuI/TBHP is described for the facile conversion of easily accessible N-allylarylamides into 5-iodomethyl-2-aryl-4,5-dihydrooxazoles in moderate to good yields. In this communication we describe CuI as the iodine source for the first time towards the intramolecular iodooxygenation of N-allylarylamides.

  DOI：

  10.1080/00397911.2017.1416142

文献信息

• A Practical Procedure for Reduction of Primary, Secondary and Tertiary Amides to Amines
  作者：Jonathan T. Reeves、Zhulin Tan、Maurice A. Marsini、Zhengxu S. Han、Yibo Xu、Diana C. Reeves、Heewon Lee、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1002/adsc.201200835

  日期：2013.1.14

  A mild and general procedure for reduction of primary, secondary, and tertiary amides using catalytic triruthenium dodecacarbonyl and 1,1,3,3‐tetramethyldisiloxane as reductant is described. The reaction is tolerant of numerous functional groups, and the amine products can often be isolated by direct crystallization as hydrochloride salts. The catalyst and silane are commercially available, air stable

  描述了使用催化的十二碳三钌和1,1,3,3-四甲基二硅氧烷作为还原剂还原伯，仲和叔酰胺的温和通用方法。该反应耐受许多官能团，并且胺产物通常可以通过直接结晶以盐酸盐的形式分离。催化剂和硅烷是可商购的，空气稳定的并且便宜的，这使得该程序可用于实验室和大规模应用。
• Synthesis of CF3-containing oxazolines via trifluoromethylation of allylamides with Togni reagent in the presence of alkali metal iodides
  作者：Shintaro Kawamura、Daisuke Sekine、Mikiko Sodeoka

  DOI：10.1016/j.jfluchem.2017.07.012

  日期：2017.11

  method for CF3-containing oxazolines via trifluoromethylation of allylamides by using Togni reagent in the presence of alkali metal iodides, which play a key role in selective production of the desired oxazoline. The reaction did not proceed efficiently with copper catalysts commonly used for oxytrifluoromethylations. Our method afforded a wide variety of CF3-containing oxazolines, which are potential candidates

  我们报告了一种有效的合成方法，通过在碱金属碘化物的存在下使用Togni试剂通过丙烯酰胺的三氟甲基化丙烯酰胺的三氟甲基化来制备含CF 3的恶唑啉，该方法在选择性生产所需的恶唑啉中起关键作用。用通常用于氧三氟甲基化的铜催化剂不能有效地进行反应。我们的方法提供了多种含CF 3的恶唑啉，它们是药物，农用化学品和功能材料的潜在候选者。
• Hypervalent Iodine-Mediated Alkene Functionalization: Oxazoline and Thiazoline Synthesis via Inter-/Intramolecular Aminohydroxylation and Thioamination
  作者：Hyeonho Jeon、Darong Kim、Ji Hoon Lee、Jaeyoung Song、Won Seok Lee、Dong Wook Kang、Soosung Kang、Seok Beom Lee、Sungwook Choi、Ki Bum Hong

  DOI：10.1002/adsc.201701087

  日期：2018.2.15

  A metal‐free oxidative difunctionalization of N‐allylamides and N‐allylthioamides has been developed. This system features the use of a hypervalent iodine oxidant with electron‐deficient amines to access 5‐amino‐oxazoline and thiazoline scaffolds under mild conditions. Notably, various electron‐deficient amines were systematically evaluated and we verified the reaction profile was originated from an

  已开发出N-烯丙酰胺和N-烯丙硫酰胺的无金属氧化双官能团。该系统的特点是在温和条件下，使用具有电子缺陷胺的高价碘氧化剂访问5-氨基恶唑啉和噻唑啉支架。值得注意的是，对各种电子不足的胺进行了系统的评估，我们证实了反应谱源于连接的（苯）磺酰基。
• <i>Exo-trig</i> selenocyclization of secondary allylic carboxamides using Woollins’ reagent: <i>en route</i> to 2,5-disubstituted selenazolines
  作者：Priyanka N. Makhal、Srinivas Reddy Dannarm、Arbaz Sujat Shaikh、Rezwan Ahmed、Shrilekha Chilvery、Lahu N. Dayare、Rajesh Sonti、Chandraiah Godugu、Venkata Rao Kaki

  DOI：10.1039/d2cc06782j

  日期：——

  We report microwave-assisted selenation and exo-trig cyclization of secondary allylic carboxamides using Woollins’ reagent, a serendipitous finding observed during an attempt to synthesize N-allylbenzoselenoamide compounds. This resulted in the first reported synthesis of 2-aryl-5-methyl selenazolines. Twenty-one diversified selenazolines and three late-stage-functionalized drug molecules were synthesized

  我们使用 Woollins 试剂报告了二级烯丙基甲酰胺的微波辅助硒化和外触发环化，这是在尝试合成N -烯丙基苯并硒酰胺化合物时观察到的偶然发现。这导致了首次报道的 2-aryl-5-methyl selenazolines 的合成。合成了 21 种多样化的硒唑啉和三种后期功能化药物分子，产率分别为 42-93% 和 25-52%，并进一步评估了它们的抗增殖活性。
• DE2720427
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