2-bromo-2-methyl-N-phenylpropanamide | 2322-45-4

• 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-2-methyl-N-phenylpropanamide
• 英文别名: 2-bromoisobutyranilide；α-bromo-α,α-dimethyl-N-phenylacetamide
• CAS: 2322-45-4
• 化学式: C₁₀H₁₂BrNO
• mdl: MFCD02751707
• 分子量: 242.115
• InChiKey: PLMADUFDYDHKTB-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  356.2±25.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-bromo-2-methyl-N-phenylpropanamide 在 hexaaquocopper(II) tetrafluoroborate 、 二氯甲烷 、 五甲基二乙烯三胺 作用下， 反应 1.0h， 以89%的产率得到2-chloro-2-methyl-N-phenylpropanamide
  参考文献：
  名称：

  在铜催化剂存在下，二氯甲烷作为 α-溴代羰基化合物的氯化试剂

  摘要：

  我们发现二氯甲烷是一种强大的氯化试剂，可用于处理 α-溴羰基酰胺、酯和酮的拥挤的 3° 和 2° Csp3-Br 键。在合适的铜配合物作为催化剂的存在下，所需的氯化在一小时内发生。对照实验表明，原位生成的 CuCl2 是一种关键的氯化剂，可与 α-溴羰基化合物和 Cu(I) 盐反应生成的 3° 或 2° 烷基自由基反应。

  DOI：

  10.1246/cl.170062
• 作为产物：
  描述：

  2-甲基-N-苯基丙酰胺 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-2-methyl-N-phenylpropanamide
  参考文献：
  名称：

  Electrochemical determination of the pKa of weak acids in N,N-dimethylformamide

  摘要：

  The electroreduction of NH-protic alpha-bromo amides in DMF generates an enolate-type base which undergoes a fast proton transfer from the parent compound (self-protonation), affording the corresponding reduced amide together with the conjugate base of the bromo amide. When an acid weaker than the bromo amide is added to the solution, a current increase in a potential region more negative than the main voltammetric reduction peak is observed under suitable conditions. The voltammetric pattern is in agreement with an unfavored protonation of the conjugate base of the starting compound by the added proton donor with regeneration of the electroactive bromo amide. The theoretical analysis of this reduction sequence has been carried out, and the voltammetric profiles have been simulated. Comparison of the experimental and simulated voltammetries led to the determination of the acidity difference, DELTA-pK(a), between the a-bromo amide and the added acid. For each alpha-bromo amide it was possible to obtain DELTA-pK(a) data ranging from 1.4 to 4.2. The use of a-bromo amides of different acidity with the same exogenous acids provided the link between the different sets of relative acidities. In this way, using six alpha-bromo amides, a relative acidity scale encompassing an overall pK(a) variation in DMF of about 10 units could be established. The relative scale was then anchored to the low pK(a) scale in DMF through both the determination of the acidity of selected acids and using a correlation between literature pK(a) data obtained in both DMF and DMSO. The application of this original electrochemical mechanism provided absolute pK(a) data in DMF ranging from about 16 to 26, i.e., a pK(a) region that is practically unexplored in this solvent.

  DOI：

  10.1021/ja00024a041

文献信息

• Ruthenium-Catalyzed <i>para</i> -Selective C−H Alkylation of Aniline Derivatives
  作者：Jamie A. Leitch、Claire L. McMullin、Andrew J. Paterson、Mary F. Mahon、Yunas Bhonoah、Christopher G. Frost

  DOI：10.1002/anie.201708961

  日期：2017.11.20

  The para‐selective C−H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N−H‐activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N−H metalation (as opposed to C−H metalation in

  本文报道了配有嘧啶辅助剂的苯胺衍生物的对位C-H烷基化反应。建议该反应通过原位形成的NH活化的环金属盐进行。实验和DFT机理研究阐明了钌催化剂的双重作用。这里的钌催化剂可通过N-H金属化经历环金属化（相对于C-H的金属化在间位-选择性过程）和形成氧化还原活性物种钌，以使位点选择性基加在对位位置。
• Construction of Vicinal Quaternary Carbons via Cu-catalyzed Dearomative Radical Addition
  作者：Naoki Tsuchiya、Takashi Nishikata

  DOI：10.1246/cl.190247

  日期：2019.7.5

  In this paper, we confirmed the dearomative addition of tertiary alkyl radicals onto BHT derivatives to form highly congested vicinal quaternary carbons to produce tert-alkylated styrenes in the pr...

  在本文中，我们证实了叔烷基与 BHT 衍生物的脱芳基加成形成高度拥挤的邻位季碳，从而在制备过程中产生叔烷基化苯乙烯。
• Iron-Enhanced Reactivity of Radicals Enables C–H Tertiary Alkylations for Construction of Functionalized Quaternary Carbons
  作者：Yu Yamane、Kohei Yoshinaga、Michinori Sumimoto、Takashi Nishikata

  DOI：10.1021/acscatal.8b04872

  日期：2019.3.1

  is one of the most attractive catalysts, especially for aromatic C–H functionalizations. However, stoichiometric amounts of oxidants and strong carbanions are required, and C–H tertiary alkylation, especially with electron-deficient alkyl groups, is unexplored. In this paper, we describe the development of iron-catalyzed selective C–H tertiary alkylations with heteroaromatics, in which an iron salt

  铁是最有吸引力的催化剂之一，特别是对于芳族CHH功能化而言。但是，需要化学计量的氧化剂和强碳负离子，并且尚未开发C–H叔烷基化，尤其是缺乏电子的烷基。在本文中，我们描述了杂芳族化合物在铁催化的选择性C–H叔烷基化反应中的发展，其中铁盐充当单电子源，并增强了由α-溴羰基化合物生成的叔烷基的反应性。我们建立的方法论已在非常简单的条件下有效合成各种季碳原子中得到了证明。
• Oxyindole derivatives
  申请人：Uchida Chikara

  公开号：US20060194842A1

  公开（公告）日：2006-08-31

  This invention relates to compounds of the formula (I): or a pharmaceutically acceptable salt thereof, wherein: A, R 1 , R 2 , R 3 , R 4 and R 5 are each as described herein or a pharmaceutically acceptable salt, and compositions containing such compounds and the use of such compounds in the treatment of a condition mediated by 5-HT 4 agonistic activity such as, but not limited to, as gastroesophageal reflux disease, gastrointestinal disease, gastric motility disorder, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome (IBS), constipation, dyspepsia, esophagitis, gastroesophageal disease, nausea, central nervous system disease, Alzheimer's disease, cognitive disorder, emesis, migraine, neurological disease, pain, cardiovascular disorders, cardiac failure, heart arrhythmia, diabetes or apnea syndrome.

  这项发明涉及以下式（I）的化合物： 或其药学上可接受的盐，其中： A，R1，R2，R3，R4和R5分别如本文所述或药学上可接受的盐，以及含有这种化合物的组合物和利用这种化合物治疗由5-HT 4 激动活性介导的疾病的用途，例如但不限于胃食管反流病、胃肠疾病、胃动力障碍、非溃疡性消化不良、功能性消化不良、肠易激综合征（IBS）、便秘、消化不良、食管炎、胃食管疾病、恶心、中枢神经系统疾病、阿尔茨海默病、认知障碍、呕吐、偏头痛、神经系统疾病、疼痛、心血管疾病、心力衰竭、心律失常、糖尿病或呼吸暂停综合征。
• Copper-Salt-Promoted Carbocyclization Reactions of α-Bromo-N-arylacylamides
  作者：Che-Ping Chuang、Ying-Yu Chen、Tsung-Han Chuang、Cheng-Hao Yang

  DOI：10.1055/s-0036-1588642

  日期：——

  Abstract A mild and convenient synthetic method for oxindoles and α-arylacylamides bearing an all carbon quaternary stereocenter from the readily available α-bromo-N-arylacylamides has been developed. This Cu(acac)2/Phen-promoted radical cyclization reaction, via the intramolecular radical cyclization onto the aryl moiety, can proceed in two different routes depending on the substituents on the nitrogen

  摘要 已经开发了一种温和且方便的合成方法，用于从容易获得的α-溴-N-芳基酰基酰胺中合成带有全碳四级立体中心的羟吲哚和α-芳基酰基酰胺。经由分子内自由基环化到芳基部分上的该Cu（acac）2 /苯酚促进的自由基环化反应可以根据氮原子上的取代基以两种不同的途径进行。在该转化中，以高化学选择性形成了羟吲哚和α-芳基酰酰胺。各种有用的官能团，例如甲氧基，氟，氯，溴，甲氧基羰基和氰基与反应条件相容。使用廉价，容易获得的Cu（acac）2和Phen使该协议非常有效和实用。 已经开发了一种温和且方便的合成方法，用于从容易获得的α-溴-N-芳基酰基酰胺中合成带有全碳四级立体中心的羟吲哚和α-芳基酰基酰胺。经由分子内自由基环化到芳基部分上的该Cu（acac）2 /苯酚促进的自由基环化反应可以根据氮原子上的取代基以两种不同的途径进行。在该转化中，以高化学选择性形成了羟吲哚和α-芳基酰酰胺。各种有用的官能团，