2-bromo-4,5-dimethoxy-N,N-dimethylbenzamide

• 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: 2-bromo-4,5-dimethoxy-N,N-dimethylbenzamide
• 英文别名: 2-bromo-N,N-dimethyl-4,5-dimethoxybenzamide
• 化学式: C₁₁H₁₄BrNO₃
• 分子量: 288.141
• InChiKey: VZOIQPHZHCCXOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硫代异氰酸苯酯 、 2-bromo-4,5-dimethoxy-N,N-dimethylbenzamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis of 3-Iminobenzo[c]thiophen-1(3H)-one Derivatives Based on the Reaction of 2-Lithio-N,N-dimethylbenzamides with Isothiocyanates

  摘要：

  A facile two-step sequence for the preparation of 3-(Z)-(aryl(oralkyl)imino)benzo[c]thiophen-1(311)-ones starting from 2-bromo-N,Ndimethylbenzamides has been developed. The starting amides were allowed to react with butyllithium to generate 2-lithio-N,N-dimethylbenzamides, of which reaction with isothiocyanates gave the corresponding N,N-dimethyl-2(thiocarbamoyl)benzamides. These precursors were treated with p-toluenesulfonic acid monohydrate. The cyclization proceeds in a chemo- and stereo -selective manner to provide the desired product as the sole isolated product in each case.

  DOI：

  10.3987/com-17-13698
• 作为产物：
  描述：

  6-溴藜芦醛 在 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 2-bromo-4,5-dimethoxy-N,N-dimethylbenzamide
  参考文献：
  名称：

  合成4,5-双（邻卤代芳基）异恶唑的简便策略

  摘要：

  可以有效地制备一系列新的1,2-双（邻卤代芳基）乙酮并将其应用于4,5-双（邻卤代芳基）异恶唑的合成。对中间体羟基异恶唑啉的分离进行了结构检查，为基于胺交换过程的杂环化机理提供了明确的证据。还描述了重要副产物（如苯甲酰胺和三芳基丙腈）的分离和X射线晶体学研究。

  DOI：

  10.1021/jo0002700

文献信息

• Copper-catalyzed amidation of benzoic acids using tetraalkylthiuram disulfides as amine sources
  作者：Meng-Tian Zeng、Wan Xu、Min Liu、Xing Liu、Cai-Zhu Chang、Hui Zhu、Zhi-Bing Dong

  DOI：10.1080/00397911.2017.1330960

  日期：2017.8.18

  method for the copper-catalyzed synthesis of N-substituted benzamides was explored. In the presence of CuBr and di-tert-butyl peroxide, various N-substituted benzamides were prepared through amidation of benzoic acid by using commercially available and cheap tetraalkylthiuram disulfides as amine sources. With this protocol, a series of 14 N-substituted benzamides were furnished in good to excellent yields

  摘要 探索了一种简便的铜催化合成 N-取代苯甲酰胺的方法。在 CuBr 和二叔丁基过氧化物的存在下，使用市售的廉价四烷基秋兰姆二硫化物作为胺源，通过苯甲酸的酰胺化制备了各种 N-取代的苯甲酰胺。使用该协议，提供了一系列 14 N 取代苯甲酰胺，产量良好。广泛的底物范围和良好的收率显示了其在有机合成中的实用合成价值。图形概要
• A Convenient Strategy for the Synthesis of 4,5-Bis(<i>o</i>-haloaryl)isoxazoles
  作者：Roberto Olivera、Raul SanMartin、Esther Domínguez、Xabier Solans、Miren Karmele Urtiaga、María Isabel Arriortua

  DOI：10.1021/jo0002700

  日期：2000.10.1

  synthesis of 4,5-bis(o-haloaryl)isoxazoles. Isolation of intermediate hydroxyisoxazolines, which are structurally examined, provides a definitive proof for a heterocyclization mechanism based on an amine exchange process. The isolation and X-ray crystallographic studies of significant side products such as benzamides and triarylpropionitriles are also described.

  可以有效地制备一系列新的1,2-双（邻卤代芳基）乙酮并将其应用于4,5-双（邻卤代芳基）异恶唑的合成。对中间体羟基异恶唑啉的分离进行了结构检查，为基于胺交换过程的杂环化机理提供了明确的证据。还描述了重要副产物（如苯甲酰胺和三芳基丙腈）的分离和X射线晶体学研究。
• Synthesis of 3-Iminobenzo[c]thiophen-1(3H)-one Derivatives Based on the Reaction of 2-Lithio-N,N-dimethylbenzamides with Isothiocyanates
  作者：Kazuhiro Kobayashi、Yuuho Shigemura、Daiki Fujiwara

  DOI：10.3987/com-17-13698

  日期：——

  A facile two-step sequence for the preparation of 3-(Z)-(aryl(oralkyl)imino)benzo[c]thiophen-1(311)-ones starting from 2-bromo-N,Ndimethylbenzamides has been developed. The starting amides were allowed to react with butyllithium to generate 2-lithio-N,N-dimethylbenzamides, of which reaction with isothiocyanates gave the corresponding N,N-dimethyl-2(thiocarbamoyl)benzamides. These precursors were treated with p-toluenesulfonic acid monohydrate. The cyclization proceeds in a chemo- and stereo -selective manner to provide the desired product as the sole isolated product in each case.