4-bromo-N-allyl-N-methyl-benzamide | 214766-83-3

• 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: 4-bromo-N-allyl-N-methyl-benzamide
• 英文别名: 4-bromo-N-methyl-N-prop-2-enylbenzamide
• CAS: 214766-83-3
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: FKTZIEQEFHPSPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.9±35.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-bromo-N-allyl-N-methyl-benzamide 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 、 氯苯 为溶剂， 反应 1.0h， 生成 Tert-butyl 3-(6-bromo-2-methyl-1-oxo-3,4-dihydroisoquinolin-4-yl)propanoate
  参考文献：
  名称：

  A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones

  摘要：

  :A variety of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones 6 can be prepared by a two step radical sequence: intermolecular xanthate transfer addition to an N-allylbenzamide followed by cyclisation onto the aromatic ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01561-5
• 作为产物：
  描述：

  N-甲基烯丙基胺 、 4-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-bromo-N-allyl-N-methyl-benzamide
  参考文献：
  名称：

  One-Step RhCl₃-Catalyzed Deprotection of Acyclic N-Allyl Amides

  摘要：

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.

  DOI：

  10.1021/jo070553t

文献信息

• Free Radical-Promoted Monochloroalkylarylation of Alkenes with Chloralkanes
  作者：Yingming Ren、Yaxin Ge、Qinqin Yan、Shiliu Chen、Yang Li、Lijun Li、Zhong-Quan Liu、Zejiang Li

  DOI：10.1021/acs.joc.1c01605

  日期：2021.9.3

  cascade cyclization of unactivated alkenes with chloralkanes, which undergoes selective activation of the α-C(sp3)–H bond of chloralkanes, provides a protocol for the synthesis of chlorinated heterocycles or polycyclic compounds. A series of radical inhibition experiments, radical capture operations, and radical clock tests were studied in this system.

  自由基引发的未活化烯烃与氯烷烃的级联环化，其经历了氯烷烃的 α-C(sp 3 )–H 键的选择性活化，为合成氯化杂环或多环化合物提供了一种方案。在该系统中研究了一系列自由基抑制实验、自由基捕获操作和自由基时钟测试。
• Construction of 3,4-Dihydroisoquinolinones and Indanones via DTBP-Promoted Oxidative Coupling of <i>N</i>-Allylbenzamides with Aromatic Aldehydes
  作者：Zhong-Qi Xu、Chao Wang、Lin Li、Lili Duan、Yue-Ming Li

  DOI：10.1021/acs.joc.8b01242

  日期：2018.9.7

  A metal-free oxidative tandem coupling of N-allylbenzamide with aryl aldehydes was realized. This method allowed the 1,2-difunctionalization of the C═C double bond in N-allylbenzamides through simultaneous formation of two C(sp2)–C(sp3) bonds. In the presence of DTBP, 4-substituted 3,4-dihydroisoquinolin-1(2H)-ones were obtained in satisfactory isolated yields. 3-Substituted indanones could also be

  实现了N-烯丙基苯甲酰胺与芳基醛的无金属氧化串联偶联。该方法允许通过同时形成两个C（sp 2）–C（sp 3）键在N-烯丙基苯甲酰胺中实现C═C双键的1,2-双官能化。在DTBP存在下，以令人满意的分离产率获得了4-取代的3，4-二氢异喹啉-1（2H）-1 。3-取代的茚满酮也可以通过改变原料的结构来形成。
• Hydroxyalkylation-Initiated Radical Cyclization of <i>N</i>-Allylbenzamide for Direct Construction of Isoquinolinone
  作者：Wei Zhou、Shengyang Ni、Haibo Mei、Jianlin Han、Yi Pan

  DOI：10.1021/acs.orglett.5b01140

  日期：2015.6.5

  A metal-free hydroxyalkylation-initiated radical six-membered heterocycle formation reaction of N-allylbenzamide is developed. This reaction proceeds through C(sp(3))H bond cleavage, oxyalkylation of the double bond, and intramolecular cyclization, which provides a new route toward 4-substituted 3,4-dihydroisoquinolin-1(2H)-one derivatives.
• One-Step RhCl₃-Catalyzed Deprotection of Acyclic <i>N</i>-Allyl Amides
  作者：Michael J. Zacuto、Feng Xu

  DOI：10.1021/jo070553t

  日期：2007.8.1

  [GRAPHICS]A convenient one-step RhCl3-catalyzed deprotection of acyclic N-allyl amides is described. Preliminary mechanistic studies reveal that the key to the success of the one-step deprotection process is the dual function of RhCl3 in alcohol solvents. Reaction of RhCl3 with n-PrOH not only provides an active rhodium hydride species to catalyze isomerization of N-allyl amides to corresponding enamides but also generates a crucial catalytic amount of HCl to convert the enamides to deallylated amides through N,O-acetal exchange.
• A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones
  作者：Nathalie Cholleton、Samir Z. Zard

  DOI：10.1016/s0040-4039(98)01561-5

  日期：1998.10

  :A variety of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones 6 can be prepared by a two step radical sequence: intermolecular xanthate transfer addition to an N-allylbenzamide followed by cyclisation onto the aromatic ring. (C) 1998 Elsevier Science Ltd. All rights reserved.