N-allyl-3-phenylpropanamide | 133055-17-1

• 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-phenylpropanamide
• 英文别名: 3-phenyl-N-prop-2-enylpropanamide
• CAS: 133055-17-1
• 化学式: C₁₂H₁₅NO
• mdl: MFCD03388903
• 分子量: 189.257
• InChiKey: CEHSOGHGUSJMQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-phenylpropanamide 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以67%的产率得到2-benzyl-4-pentenenitrile
  参考文献：
  名称：

  Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction

  摘要：

  An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile products in moderate to excellent yields. The scope and versatility of this reaction are demonstrated by its use on a wide variety of substrates, including nitrogen- and oxygen-substituted amides. The rearrangements of cis- and trans-4-tert-butyl-N-allylcyclohexanecarboxamides 16a and 16b are reported and were found to give a ratio of axial to equatorial (A:E) products consistent with A:E ratios found for other related sigmatropic reactions. The stereochemical requirements for this reaction appear to be similar to other [3,3]-rearrangements even though the transition state for this rearrangement is most likely neither boat nor chairlike.

  DOI：

  10.1021/jo951587g
• 作为产物：
  描述：

  3-苯基丙酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 N-allyl-3-phenylpropanamide
  参考文献：
  名称：

  Regioselective Dearomative Amidoximation of Nonactivated Arenes Enabled by Photohomolytic Cleavage of N‐nitrosamides

  摘要：

  摘要脱芳基螺环化反应是将烷烃转化为三维结构的一种很有前景的方法；然而，控制非活化烷烃脱芳基反应的区域选择性，以获得螺环化的 1,2-二官能度，而不是其动力学上偏好的 1,4-二官能度，却极具挑战性。在这里，我们揭示了一种新策略，即通过可见光直接诱导亚硝酰胺的 N-NO 键的均裂，实现（杂）烷的 1,2- 或 1,4- 氨基肟化，从而产生各种高区域选择性的氨基肟化螺环，而这些螺环以前是无法获得的，或者需要精心的合成工作。通过对照实验和密度泛函理论计算，研究了观察到的区域选择性的机理和起源。

  DOI：

  10.1002/anie.202317968

文献信息

• Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
  作者：Céline Guissart、Andre Barros、Luis Rosa Barata、Gwilherm Evano

  DOI：10.1021/acs.orglett.8b01896

  日期：2018.9.7

  An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted

  报道了一种在温和条件下将酰亚胺转化为一系列羧酸衍生物的有效，广泛适用，操作简单和发散的方法。通过简单地使用催化量的镱（III），三氟甲磺酸，如醇的存在下，路易斯酸的启动子，水，胺，或Ñ，Ô -dimethylhydroxylamine，宽范围的酰亚胺是平滑且容易地转化为相应的酯，羧酸，酰胺和Weinreb酰胺的收率很高。该方法尤其使得容易裂解基于恶唑烷酮的助剂。
• Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
  作者：P. Veeraraghavan Ramachandran、Henry J. Hamann、Shivani Choudhary

  DOI：10.1021/acs.orglett.0c03184

  日期：2020.11.6

  Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities

  胺-硼烷用作直接酰胺化的两用试剂，可活化脂肪族和芳香族羧酸，随后以高达99％的收率递送胺以提供相应的酰胺。气态或低沸点胺作为硼烷络合物的输送提供了优于现有方法的主要优势。利用含有硼烷不相容官能团的胺-硼烷可以制备官能化的酰胺。提出了通过三酰氧基硼烷-胺络合物的分子间机制。
• Direct Amidation from Alcohols and Amines through a Tandem Oxidation Process Catalyzed by Heterogeneous‐Polymer‐Incarcerated Gold Nanoparticles under Aerobic Conditions
  作者：Jean‐François Soulé、Hiroyuki Miyamura、Shū Kobayashi

  DOI：10.1002/asia.201300733

  日期：2013.11

  highly elegant and suitable synthesis of amide products from alcohols and amines through a tandem oxidation process that uses molecular oxygen as a terminal oxidant. Carbon‐black‐stabilized polymer‐incarcerated gold (PICB‐Au) or gold/cobalt (PICB‐Au/Co) nanoparticles were employed as an efficient heterogeneous catalyst depending on alcohol reactivity and generated only water as the major co‐product

  我们在本文中描述了通过串联氧化法从醇和胺中高度优雅和合适地合成酰胺产物，所述串联氧化法使用分子氧作为末端氧化剂。碳黑稳定的聚合物包埋的金（PICB-Au）或金/钴（PICB-Au / Co）纳米颗粒被用作有效的非均相催化剂，具体取决于醇的反应性，并且仅生成水作为反应的主要副产物。通过42个示例显示了广泛的基材适用性。通过使用简单的操作，可以在不损失活性的情况下回收和再利用催化剂。
• Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates
  作者：Shuai Zheng、David N. Primer、Gary A. Molander

  DOI：10.1021/acscatal.7b02795

  日期：2017.11.3

  A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent

  报道了烷基硅酸酯试剂与烷基/芳基异氰酸酯之间的镍/光氧化还原双催化酰胺化反应。与先前报道的还原偶联过程相反，该方案的特征在于反应条件温和且不存在化学计量的还原剂。基于文献的先例并通过实验结果进一步验证，提出了一种涉及异氰酸镍加合物的机理假说。
• Efficient Tandem Process for the Catalytic Deprotection of N-Allyl Amides and Lactams in Aqueous Media: A Novel Application of the Bis(allyl)–Ruthenium(IV) Catalysts [Ru(η3:η2:η3-C12H18)Cl2] and [{Ru(η3:η3-C10H16)(μ-Cl)Cl}2]
  作者：Victorio Cadierno、José Gimeno、Noel Nebra

  DOI：10.1002/chem.200700477

  日期：2007.8.6

  highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(eta(3):eta(2):eta(3)-C(12)H(18))Cl(2)] (C(12)H(18)=dodeca-2,6,10-triene-1,12-diyl) and [Ru(eta(3):eta(3)-C(10)H(16))(micro-Cl)Cl}(2)] (C(10)H(16)=2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which

  通过使用市售的双（烯丙基）-钌（IV）催化剂[Ru（eta（3）：eta（2）： eta（3）-C（12）H（18））Cl（2）]（C（12）H（18）= dodeca-2,6,10-triene-1,12-diyl）和[Ru（ eta（3）：eta（3）-C（10）H（16））（micro-Cl）Cl}（2）]（C（10）H（16）= 2,7-二甲基辛基-2,6-二烯-1,8-二基）。串联过程发生在水性介质中并以一锅法进行，涉及烯丙基单元的C = C键的初始异构化和随后生成的烯酰胺的氧化裂解。