N-butyl-2-bromopropanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-butyl-2-bromopropanamide
• 英文别名: 2-bromo-N-butylpropanamide；N-n-butyl-2-bromopropionamide；2-bromo-propionic acid butylamide；N-Butyl-2-brom-propionamid；2-Brom-propionsaeure-butylamid
• 化学式: C₇H₁₄BrNO
• 分子量: 208.098
• InChiKey: BETBSAMQQJPHJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-butyl-2-bromopropanamide 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 反应 3.5h， 生成 N-butyl-2-(4-methylsulfanyl-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl)sulfanylpropanamide
  参考文献：
  名称：

  1-Phenylpyrazolo[3,4- d ]pyrimidines; structure–activity relationships for C6 substituents at A 1 and A 2A adenosine receptors

  摘要：

  Substitution of 1-phenylpyrazolo[3,4-d]pyrimidines at C6 with N-alkyl-2-thiopropionamide groups has resulted in a series of 18 compounds which have been evaluated for binding at A(1) and A(2A) adenosine receptors. introduction of an N-ethyl group gave increased affinity at both A(1) and A(2A) receptors for the amino compound 7b compared to the primary amide 7a. An additional hydrophobic pocket exists for substituents on the amide. This pocket allows an N-ethyl group for increased affinity at both A(1) and A(2A) receptors, allows larger alkyl groups at A(2A) receptors but not at A(1) receptors and there is an H-bond interaction requiring one H-bond donor. Molecular modeling studies have also enabled a proposal of the amino acid residues involved in ligand binding at both the A(1) and A(2A) receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00190-5
• 作为产物：
  描述：

  正丁胺 、 2-溴丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 N-butyl-2-bromopropanamide
  参考文献：
  名称：

  无金属条件下苯酚的直接胺化

  摘要：

  在此，我们公开了通过使用胺化试剂直接胺化苯酚来无金属合成芳胺。该反应过程使用容易获得的胺化试剂，并为具有各种官能度的广泛芳胺提供了一种通用的合成途径，收率良好至极好。通过使用胺化和氧化偶联反应的两步路线，我们从两种市售酚类合成了三种天然存在的咔唑生物碱：murrayafoline A、mukonine 和黄花碱。

  DOI：

  10.1055/s-0033-1338703

文献信息

• Switchable Smiles Rearrangement for Enantioselective <i>O</i>-Aryl Amination
  作者：Xihao Chang、Qinglin Zhang、Chang Guo

  DOI：10.1021/acs.orglett.9b01848

  日期：2019.6.21

  atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselective amination reactions of O-arenes provides access to nonsymmetric 2′-amino[1,1′-binaphthalen]-2-ol (i.e., NOBIN-type) and [1,1′-binaphthalene]-2,2′-diamine (i.e., BINAM-type)

  由丰富且容易获得的前体组成的对映异构体苯胺的不对称组装是有机合成中最具挑战性但最有价值的过程之一。使用高效的Smiles重排完成O-芳烃的可切换对映选择性胺化反应，可得到非对称的2'-氨基[1,1'-双萘] -2-ol（即NOBIN型）和[1,1' -双萘] -2,2'-二胺（即BINAM型）衍生物。这种无过渡金属的策略提供了一种强大的途径，可以访问各种先进的高度功能化的对映体丰富的苯胺。
• Nickel-Catalyzed Stereoselective Dicarbofunctionalization of Alkynes
  作者：Zhaodong Li、Andrés García-Domínguez、Cristina Nevado

  DOI：10.1002/anie.201601296

  日期：2016.6.6

  A nickel‐catalyzed three‐component reaction involving terminal alkynes, boronic acids, and alkyl halides is presented herein. Trisubstituted alkenes can be obtained in a highly regio‐ and stereocontrolled manner by the simultaneous addition of both aryl and alkyl groups across the triple bond in a radical‐mediated process. The reaction, devoid of air‐ and moisture‐sensitive organometallic reagents

  本文介绍了镍催化的三组分反应，涉及末端炔烃，硼酸和卤代烷。通过在自由基介导的过程中通过三键同时添加芳基和烷基，可以以高度区域控制和立体控制的方式获得三取代烯烃。该反应不含对空气和湿气敏感的有机金属试剂和催化剂，操作简单，具有宽泛的范围和对官能团的耐受性。
• Cooperative Ligand-Promoted P^(III)-Directed Ruthenium-Catalyzed Remote <i>Meta</i>-C–H Alkylation of Tertiary Phosphines
  作者：Zheng-Xin Zhou、Jia-Wei Li、Liang-Neng Wang、Ming Li、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1021/acs.orglett.1c00237

  日期：2021.3.19

  ruthenium-catalyzed meta-selective C–H activation of phosphines by using intrinsic P(III) as a directing group. 2,2,6,6-Tetramethylheptane-3,5-dione acts as the ligand and exhibits an excellent performance in boosting the meta-alkylation. The protocol allows an efficient and straightforward synthesis of meta-alkylated tertiary phosphines. Several meta-alkylated phosphines were evaluated for Pd-catalyzed Suzuki coupling

  在本文中，我们公开了钌催化的元通过使用固有的P.膦-选择性C-H活化（III）作为定向基团。2,2,6,6-四甲基庚烷-3,5-二酮充当配体并在促进间位烷基化方面表现出出色的性能。该方案允许间位烷基化的叔膦的有效而直接的合成。评估了几种间位烷基化的膦在Pd催化的Suzuki偶联中的作用，发现其优于市售的邻位取代的膦。通过双官能化膦的合成进一步证明了该方法的实用性。
• Diastereoselective α-alkoxylation of lactamide N-alkyl groups via intramolecular formation of oxonium ions as the key intermediate
  作者：Tohru Kamada、Akira Oku

  DOI：10.1039/a805638b

  日期：——

  Stereoselective introduction of an alkoxy group to the amine unit of lactamide derivatives, under electrochemical oxidation conditions, was investigated based upon the assumption that a cyclic oxonium ion can be formed between the alkoxy substituent on the chiral center and a carbocation generated at the α-position of N-alkyl substituents. With N-monosubstituted lactamides, diastereoselectivity in the N-α-alkoxylated product was not observed. With N,N-disubstituted lactamides, however, the selectivity appeared though in low ratios (≈2.2). Requisite factors that govern the stereoselectivity, i.e. nucleophilicity of both internal and external nucleophiles and substitution on amine units, were also examined.

  在研究电化学氧化条件下，氨基酸酰胺衍生物的醇氧基团的立体选择性引入时，假设在手性中心的醇氧基取代基与在N-烷基取代基的α位生成的碳正离子之间可以形成循环氧鎓离子。对于N-单取代的酰胺类化合物，在N-α-醇氧基化产物中没有观察到二芴选择性。然而，对于N,N-二取代的酰胺类化合物，尽管选择性很低（≈2.2），但还是出现了选择性。还研究了影响立体选择性的必要因素，即内部和外部亲核试剂的亲核性以及氨基单元的取代情况。
• Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary α-Carbonyl Alkyl Bromides
  作者：Chao Liu、Shan Tang、Dong Liu、Jiwen Yuan、Liwei Zheng、Lingkui Meng、Aiwen Lei

  DOI：10.1002/anie.201108350

  日期：2012.4.10

  Ni made it! A novel Heck‐type reaction of secondary and tertiary α‐carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1‐diaryl alkenes were utilized as substrates to easily construct α‐alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving NiI/NiII is proposed

  倪做到了！通过使用镍催化剂，实现了仲和叔α-羰基烷基溴化物的新型Heck型反应，最有可能涉及自由基过程。各种取代的苯乙烯和1,1-二芳基烯烃被用作底物，以轻松构建具有叔碳或季碳中心的α-烯基羰基化合物。基于我们的实验结果，提出了涉及Ni I / Ni II的催化循环。EWG =吸电子基团。