N-allyl-4-(1,1-dimethylethyl)benzamide

• 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-4-(1,1-dimethylethyl)benzamide
• 英文别名: N-allyl-4-(tert-butyl)benzamide；4-tert-butyl-N-(prop-2-en-1-yl)benzamide；4-tert-butyl-N-prop-2-enylbenzamide
• 化学式: C₁₄H₁₉NO
• mdl: MFCD01072692
• 分子量: 217.311
• InChiKey: GTLXSPCXLGSZOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 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-4-(1,1-dimethylethyl)benzamide 在 triethylamine pentahydrogen fluoride salt 、 4-碘甲苯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以66%的产率得到5-(fluoromethyl)-2-(4-(1,1-dimethylethyl)phenyl)-oxazoline
  参考文献：
  名称：

  Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator

  摘要：

  A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of Et3N center dot 5HF and mediates the cyclization of N-allylcarboxamide to 5-fluoromethyl-2-oxazoline. This method allows application to various substrates furnishing the 2-oxazolines with yields up to 68%. The protocol is easy to conduct under constant current conditions offering a sustainable alternative over conventional reagent-based pathways.

  DOI：

  10.1021/acs.orglett.8b03682
• 作为产物：
  描述：

  对叔丁基苯甲酸 、 丙烯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-allyl-4-(1,1-dimethylethyl)benzamide
  参考文献：
  名称：

  N-烯丙基甲酰胺的电化学氧化环化：有效合成卤代恶唑啉

  摘要：

  在此，我们报道了一种有效且可持续的N-烯丙基甲酰胺分子内电化学环化，用于合成各种卤代恶唑啉。该方法是在一个简单的未分隔的电池中进行的，使用锂卤盐作为氧化还原介质和卤素源。在室温下以中等至良好的产率构建了多种恶唑啉，包括五元和六元杂环以及碘、溴和氯甲基恶唑啉。值得注意的是，这种电化学氧化环化避免了使用外部氧化剂。

  DOI：

  10.1039/d1nj04819h

文献信息

• Electrochemical Chalcogenation of <i>β,γ</i> ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
  作者：Samrat Mallick、Mrinmay Baidya、Kingshuk Mahanty、Debabrata Maiti、Suman De Sarkar

  DOI：10.1002/adsc.201901262

  日期：2020.3.4

  The current report represents a transition‐metal‐free synthesis of oxazoline and isoxazoline derivatives by a tandem electro‐oxidative chalcogenation‐cyclization process. Both C−Se and C−S bond‐forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline

  本报告显示了通过串联电氧化硫属元素化-环化过程的无过渡金属合成恶唑啉和异恶唑啉衍生物。C-Se和C-S键形成方案均不使用任何外部氧化剂而开发，并且反应在室温下进行，并且对空气开放。使用这种方法，合成了29个取代的恶唑啉和16个取代的异恶唑啉衍生物，分离产率高达91％。
• CuBr 2 -promoted intramolecular bromocyclization of N-allylamides and aryl allyl ketone oximes
  作者：Chun-Hua Yang、Zhong-Qi Xu、Lili Duan、Yue-Ming Li

  DOI：10.1016/j.tet.2017.10.025

  日期：2017.11

  A new and easy-to-perform route to 2-oxazolines amd isoxazolines was reported. Using CuBr2 as both the bromide source and the reaction promoter, bromocyclization of N-allylamides and allyl ketone oximes proceeded readily, leading to oxazolines and isoxazolines in good to excellent yields.

  据报道，有一条新的且易于执行的方法合成2-恶唑啉和异恶唑啉。使用CuBr 2作为溴化物源和反应促进剂，N-烯丙酰胺和烯丙基酮肟的溴环化反应容易进行，从而产生了恶唑啉和异恶唑啉，收率良好至极佳。
• 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。
• Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)₂-Promoted Intramolecular Halooxygenation of <i>N</i>-Allylcarboxamides
  作者：Gong-Qing Liu、Chun-Hua Yang、Yue-Ming Li

  DOI：10.1021/acs.joc.5b01832

  日期：2015.11.20

  A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading : to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.
• CuI/TBHP: A versatile reagent system for the synthesis of 5-iodomethyl-2-aryl-4,5-dihydrooxazoles from <i>N</i>-allylarylamides
  作者：Kare Nagaraju、Nomula Rajesh、Palakodety Radha Krishna

  DOI：10.1080/00397911.2017.1416142

  日期：2018.5.3

  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.