N-烯丙基-N-苯基苯甲酰胺 | 6391-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-烯丙基-N-苯基苯甲酰胺
• 英文名称: N-allyl-N-phenylbenzamide
• 英文别名: n-Allyl-n-benzoyl aniline；N-phenyl-N-prop-2-enylbenzamide
• CAS: 6391-89-5
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: VTZIMSJTCWSECN-UHFFFAOYSA-N

物化性质

• 沸点：
  134-138 °C(Press: 0.6 Torr)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-烯丙基-N-苯基苯甲酰胺 在 偶氮二异丁腈 、 三苯基氢化锡 、 水 作用下， 以 苯 为溶剂， 反应 2.75h， 生成 benzoic acid-(β-anilino-isopropyl ester)
  参考文献：
  名称：

  Functional group manipulation via organoselenium- and halogen-induced cyclofunctionalization/hydrolysis of allylic benzimidates, tertiary benzamides, and benzamidines. Regioflexible synthesis of amino alcohol derivatives

  摘要：

  Allylic benzimidates were treated with benzeneselenenyl halides in chloroform or acetonitrile to give, via 5-exo cyclofunctionalization/hydrolysis, 3-(benzoyloxy)-2-(phenylamino)-1-(phenylselenenyl)-alkanes in fair yields. Allylic tertiary benzamides afforded 2-(benzoyloxy)-3-(phenylamino)-1-(phenylselenenyl)alkanes when submitted to similar reaction conditions. Bromoalkanes, functionalized in an analogous way, were obtained after hydrolytic workup when bromine was added to allylic benzimidates and tertiary benzamides. In some of these reactions, products of 6-endo cyclofunctionalization/hydrolysis (1-(benzoyloxy)-3-(phenylamino)-2-bromoalkanes) were also formed. The addition of benzeneselenenyl bromide to some a-substituted allylic benzimidates and tertiary benzamides was diastereoselective (0 < de < 90%, depending on conditions) with a preference for threo isomer formation. Hydrodeselenation/hydrodebromination of the cyclofunctionalization/hydrolysis products was efficiently effected (88-100% yield) by treatment of the products with triphenyltin hydride in refluxing benzene containing a catalytic amount of azobis(isobutyronitrile). The proper choice of allylic benzimidate/tertiary benzamide allowed the preparation of amino alcohol derivatives in which the 1,2-orientation of the functional groups, relative to the carbon backbone, could be varied in a controlled and predictable manner. The regioflexibility of the process was demonstrated for primary, secondary, and tertiary positions. When allylic benzamidines were submitted to the cyclofunctionalization/hydrolysis reaction conditions using benzeneselenenyl bromide as the electrophilic reagent, 5-phenylselenenyl(methyl) -substituted dihydroimidazoles were obtained.

  DOI：

  10.1021/jo00061a009
• 作为产物：
  描述：

  N-苯基亚胺苄基氯 在 苯 作用下， 生成 N-烯丙基-N-苯基苯甲酰胺
  参考文献：
  名称：

  Mumm; Moeller, Chemische Berichte, 1937, vol. 70, p. 2214,2226

  摘要：

  DOI：

文献信息

• Regio- and Stereoselective (SN2) N-, O-, C- and S-Alkylation Using Trialkyl Phosphates
  作者：Amit Banerjee、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1055/a-1504-8366

  日期：2023.1

  Bimolecular nucleophilic substitution (SN2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic

  双分子亲核取代 (SN2) 是有机化学中最著名的基本反应之一，用于从两个分子生成新分子。原则上，亲核试剂从具有合适离去基团（最常见的是卤化物）的烷化剂的背面攻击。然而，烷基卤价格昂贵、非常有害、有毒且不稳定，这使得它们在实验室使用中存在问题。相比之下，磷酸三烷基酯价格低廉、易于获得且在室温、空气中稳定且易于处理，但很少用作有机合成中的烷基化剂。在这里，我们描述了一种使用现成的磷酸三烷基酯对各种 N-、O-、C- 和 S-亲核试剂进行亲核烷基化的温和、直接和强大的方法。反应以优异的收率顺利进行，和定量产量在许多情况下，并涵盖广泛的底物。此外，通过手性中心构型的反转（高达 98% ee）实现了仲烷基的罕见立体选择性转移。
• MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
  申请人：Dow AgroSciences LLC

  公开号：US20170208803A1

  公开（公告）日：2017-07-27

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的组合物，以及使用这种分子和组合物对抗这些害虫的过程。这些分子和组合物可以用作杀螨剂、杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂。本文件披露了具有以下式（“式一”）的分子。
• Nickel(0)-Catalyzed<i>N</i>-Allylation of Amides and<i>p</i>-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions
  作者：Mohamed Salah Azizi、Youssef Edder、Abdallah Karim、Mathieu Sauthier

  DOI：10.1002/ejoc.201600500

  日期：2016.8

  Nickel(0)-catalyzed direct N-allylation of amides and p-toluenesulfonamide with allylic alcohols took place in the presence of Ni0–diphosphine complexes. The corresponding N-allylated (and/or N,N-diallylated) products were obtained in moderate to high yields under neutral conditions.

  镍（0）催化酰胺和对甲苯磺酰胺与烯丙醇的直接 N-烯丙基化发生在 Ni0-二膦配合物的存在下。在中性条件下以中等至高产率获得相应的 N-烯丙基化（和/或 N,N-二烯丙基化）产物。
• REARRANGEMENT OF ALLYLIC<i>N</i>-PHENYLFORMIMIDATES TO<i>N</i>-ALLYL-<i>N</i>-PHENYLFORMAMIDES CATALYZED BY PALLADIUM COMPLEXES
  作者：Takao Ikariya、Yasutoshi Ishikawa、Kiyomiki Hirai、Sadao Yoshikawa

  DOI：10.1246/cl.1982.1815

  日期：1982.11.5

  The palladium complexes such as Pd(PPh3)4 and Pd(PhCN)2Cl2 catalyzed the rearrangement of allylic N-phenylformimidates to give N-allyl-N-phenylformamides under a mild condition. The reaction courses are strongly influenced by the oxidation state of palladium complexes used.

  钯配合物如 Pd(PPh3)4 和 Pd(PhCN)2Cl2 在温和条件下催化烯丙基 N-苯基甲酰亚胺重排生成 N-烯丙基-N-苯基甲酰胺。反应过程受所用钯配合物的氧化态影响很大。
• Combined Effect of Palladium Catalyst and the Alcohol to Promote the Uncommon Bis‐Alkoxycarbonylation of Allylic Substrates
  作者：Diego Olivieri、Riccardo Tarroni、Nicola Della Ca'、Raffaella Mancuso、Bartolo Gabriele、Gilberto Spadoni、Carla Carfagna

  DOI：10.1002/cctc.202101923

  日期：2022.3.22

  access to useful 2-substituted succinates was achieved starting from various allyl derivatives, including allyl carbonates, under mild conditions. The selectivity of this Pd-catalyzed oxidative Bis-Alkoxycarbonylation is governed by the combined effect of the ligand (anthryl α-diimine) and the nucleophile (benzyl alcohol). Mechanistic insights, based on DFT calculations, were proposed.

  在温和条件下，从各种烯丙基衍生物（包括碳酸烯丙酯）开始，可以轻松、意外地获得有用的 2-取代琥珀酸酯。这种 Pd 催化的氧化双烷氧基羰基化的选择性受配体（蒽基 α-二亚胺）和亲核试剂（苯甲醇）的联合作用控制。提出了基于 DFT 计算的机械见解。