N-(2-methylallyl)-N-phenylbenzamide | 147428-18-0

• 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-(2-methylallyl)-N-phenylbenzamide
• 英文别名: N-phenyl-N-(2-methylallyl)benzamide；N-(2-methylprop-2-enyl)-N-phenylbenzamide
• CAS: 147428-18-0
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: UTYZKXOJWQOTFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-(2-methylallyl)-N-phenylbenzamide 在 水 、 溴 作用下， 生成 2-(benzoyloxy)-2-methyl-3-(phenylamino)-1-bromopropane
  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：

  2-methylallyl N-phenylbenzimidate 以91%的产率得到N-(2-methylallyl)-N-phenylbenzamide
  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

文献信息

• Cascade alkylarylation of substituted <i>N</i>-allylbenzamides for the construction of dihydroisoquinolin-1(2<i>H</i>)-ones and isoquinoline-1,3(2<i>H</i>,4<i>H</i>)-diones
  作者：Ping Qian、Bingnan Du、Wei Jiao、Haibo Mei、Jianlin Han、Yi Pan

  DOI：10.3762/bjoc.12.32

  日期：——

  An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C-C double bond was found to play a key role for the progress of the reaction to give the expected

  已经开发出一种以N-烯丙基酰胺衍生物为原料合成4-烷基取代的二氢异喹啉-1（2H）-的氧化反应。自由基烷基芳基化反应通过一系列烷基化和分子内环化反应进行。发现CC双键上的取代基对于反应的进行起关键作用，以提供具有良好化学收率的预期产物。另外，N-甲基丙烯腈苯甲酰胺也是当前反应的合适底物，并以良好的收率提供了烷基取代的异喹啉-1,3（2H，4H）-二酮。
• 一种2,2-二取代茚满酮化合物的合成方法
  申请人：常州大学

  公开号：CN110330442A

  公开（公告）日：2019-10-15

  本发明属于医药、有机化工及精细化工领域，具体公开了一种合成2,2‑二取代茚满酮化合物的方法。该方法的具体合成步骤如下：以N‑(2‑甲基烯丙基)酰胺化合物及3‑氨基吲唑化合物为原料，在氮气保护，铜盐催化剂、氧化剂和水的参与下，乙腈溶剂中50‑100℃的加热反应条件下，历时5‑15小时合成2,2‑二取代茚满酮化合物。该反应经历了脱氮、自由基加成、水解过程，涉及两个C‑N键的断裂和两个C‑C键的形成过程。本发明方法为茚满酮结构的合成开创了新的途径。
• 一种氰烷基取代二氢异喹啉酮化合物及其制 备方法
  申请人：江苏理工学院

  公开号：CN110194739B

  公开（公告）日：2020-12-08

  本发明涉及一种氰烷基取代二氢异喹啉酮化合物及其制备方法，以N‑烯丙基苯甲酰胺为原料，以有机腈为溶剂和氰烷基来源，在银盐氧化剂作用下，100‑150℃加热反应10‑24小时发生加成、环化反应，最终后处理得到所述氰烷基取代二氢异喹啉酮化合物。本发明方法不需要添加其他反应溶剂，反应体系较简单，以银盐催化氧化，反应平稳，易于控制，简单高效，所用原材料有机腈和银盐氧化剂较便宜，且本发明的方法安全性大大提高，具有重要的应用价值。
• Pd-Catalyzed Arylperfluoroalkylation of Unactivated Olefins for the Synthesis of Heterocycles
  作者：Jinhua Zheng、Pan Chen、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1021/acs.joc.7b00598

  日期：2017.6.2

  An efficient and highly practical palladium-catalyzed arylperfluoroalkylation of unactivated olefins is presented here. A variety of perfluoroalkylated heterocyclic derivatives can be obtained in high regioselectivity. The reaction proceeds mildly without the electronic activation of the aryl group and features high generality, low-cost fluoroalkylated sources and good functional-group compatibility

  本文介绍了未活化烯烃的高效且高度实用的钯催化的芳基全氟烷基化反应。可以高区域选择性获得各种全氟烷基化的杂环衍生物。该反应温和地进行，没有芳基的电子活化，并且具有高通用性，低成本的氟代烷基化来源和良好的官能团相容性。
• Copper-promoted difunctionalization of unactivated alkenes with silanes
  作者：Yingying Xue、Zhuangzhuang Guo、Xiaoyu Chen、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1039/d1ob02318g

  日期：——

  difunctionalization of N-allyl anilines toward the synthesis of silylated indolines using commercially available silanes has been reported. This strategy provides a new avenue for the synthesis of a diverse array of indolines in reasonable yields. Preliminary mechanistic investigations indicate that the reaction probably proceeds via a radical pathway with unactivated alkenes as radical acceptors and simple silanes

  已经报道了使用市售硅烷对N-烯丙基苯胺进行有效的铜催化级联双官能化以合成甲硅烷基化二氢吲哚。该策略为以合理产率合成多种二氢吲哚提供了新途径。初步机理研究表明，该反应可能通过自由基途径进行，未活化的烯烃作为自由基受体，简单的硅烷作为自由基前体。该协议以其原子经济性、广泛的底物范围和现成的起始材料而著称。