1-(4-溴苯甲酰基)-4-甲基哌啶 | 329713-82-8

• 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: 1-(4-溴苯甲酰基)-4-甲基哌啶
• 英文名称: (4-bromophenyl)(4-methylpiperidin-1-yl)methanone
• 英文别名: 1-(4-Bromobenzoyl)-4-methylpiperidine；(4-bromophenyl)-(4-methylpiperidin-1-yl)methanone
• CAS: 329713-82-8
• 化学式: C₁₃H₁₆BrNO
• mdl: MFCD00783631
• 分子量: 282.18
• InChiKey: AERDAUHOGLBWMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基哌啶 、 4-溴苯胺 在 盐酸 、 甲烷磺酸 、 三(邻甲基苯基)磷 、 palladium dichloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 18.67h， 生成 1-(4-溴苯甲酰基)-4-甲基哌啶
  参考文献：
  名称：

  N₂ Extrusion and CO Insertion: A Novel Palladium-Catalyzed Carbonylative Transformation of Aryltriazenes

  摘要：

  A novel procedure for the replacement of N-2 with CO of aryltriazenes has been developed. Aryltriazenes were converted to the corresponding arylamides catalyzed by 1 mol % of PdCl2/P(o-Tol)(3) under CO pressure. In this process, aryldiazonium salts were generated in the presence of 40 mol % of MeSO3H. Nitrogen was released from the substrates and CO formally inserted. Aryl bromides, iodides, alkynes, and free hydroxyl groups can be tolerated in this transformation.

  DOI：

  10.1021/acs.orglett.5b00603

文献信息

• Aminocarbonylations Employing Mo(CO)₆ and a Bridged Two-Vial System: Allowing the Use of Nitro Group Substituted Aryl Iodides and Aryl Bromides
  作者：Patrik Nordeman、Luke R. Odell、Mats Larhed

  DOI：10.1021/jo302322w

  日期：2012.12.21

  A bridged two-vial system aminocarbonylation protocol where Mo(CO)6 functions as an external in situ solid source of CO has been developed. For the first time both nitro group containing aryl/heteroaryl iodides and bromides gave good to excellent yields in the Mo(CO)6-mediated and palladium(0)-catalyzed conversion to benzamides, while the identical one-vessel protocol afforded extensive reduction of

  已开发了桥接的两瓶系统氨基羰基化方案，其中Mo（CO）6用作外部原位CO固体源。含硝基的芳基/杂芳基碘化物和溴化物都首次在Mo（CO）6介导的和钯（0）催化的转化为苯甲酰胺的过程中获得了优异的优异收率，而相同的单容器实验方案则大大降低了硝基功能。上述桥连的两室方案在65–85°C反应温度下对伯胺和仲胺以及迟钝的苯胺亲核试剂均提供了良好的结果。
• NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction
  作者：Tanawat Rerkrachaneekorn、Theeranon Tankam、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1016/j.tetlet.2021.153017

  日期：2021.4

  process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed

  在这项研究中，我们开发了一种温和的电化学工艺，用于将苯甲醇/芳香醛与环胺氧化酰胺化成相应的苯甲酰胺。这种电有机合成方法在环境温度下在未分割的电池中使用 NaI 作为氧化还原介质，提供了超过 25 个中等到良好产率的酰胺产品示例。该反应的优点包括一锅合成、露天条件、在水性介质中进行，并且不需要外部导电盐、碱和氧化剂。
• N₂ Extrusion and CO Insertion: A Novel Palladium-Catalyzed Carbonylative Transformation of Aryltriazenes
  作者：Wanfang Li、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.5b00603

  日期：2015.4.17

  A novel procedure for the replacement of N-2 with CO of aryltriazenes has been developed. Aryltriazenes were converted to the corresponding arylamides catalyzed by 1 mol % of PdCl2/P(o-Tol)(3) under CO pressure. In this process, aryldiazonium salts were generated in the presence of 40 mol % of MeSO3H. Nitrogen was released from the substrates and CO formally inserted. Aryl bromides, iodides, alkynes, and free hydroxyl groups can be tolerated in this transformation.