2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)acetamide | 28217-73-4

• 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: 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)acetamide
• 英文别名: 1-bromo-5-hydroxy-4,4-dimethylpentan-2-one；N-(1-hydroxy-2-methylprop-2-yl)-2-bromoacetamide
• CAS: 28217-73-4
• 化学式: C₆H₁₂BrNO₂
• 分子量: 210.071
• InChiKey: PQCDSUUAHSANKM-UHFFFAOYSA-N

物化性质

• 沸点：
  344.7±27.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)acetamide 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 以50%的产率得到2-(bromomethyl)-4,4-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Preparation of Functionalized Oxazolines

  摘要：

  The preparation of several oxazolines substituted at C-2 by an hetero substituted methyl group is reported. 2-Aminomethyl, 2-azidomethyl, 2-nitromethyl and 2-hydroxymethyl oxazolines were obtained by substitution of the corresponding 2-halogenomethyl oxazolines. On the other hand, 2-benzyloxycarbonylaminomethyl, 2-thiophenylmethyl, 2-selenophenylmethyl oxazolines were prepared by condensation of the appropriate iminoether with a beta-aminoalcohol.

  DOI：

  10.1080/00397919208021650
• 作为产物：
  描述：

  Bromo-acetic acid 2-(2-bromo-acetylamino)-2-methyl-propyl ester 以81%的产率得到2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)acetamide
  参考文献：
  名称：

  Preparation of Functionalized Oxazolines

  摘要：

  The preparation of several oxazolines substituted at C-2 by an hetero substituted methyl group is reported. 2-Aminomethyl, 2-azidomethyl, 2-nitromethyl and 2-hydroxymethyl oxazolines were obtained by substitution of the corresponding 2-halogenomethyl oxazolines. On the other hand, 2-benzyloxycarbonylaminomethyl, 2-thiophenylmethyl, 2-selenophenylmethyl oxazolines were prepared by condensation of the appropriate iminoether with a beta-aminoalcohol.

  DOI：

  10.1080/00397919208021650

文献信息

• Synthesis and Evaluation of Non-peptidic Cysteine Protease Inhibitors of P. falciparum Derived from Etacrynic Acid
  作者：Marie-Adrienne Dude、Ulrich Kaeppler、Monika Herb、Markus Schiller、Franziska Schulz、Birgit Vedder、Saskia Heppner、Gabriele Pradel、Jiri Gut、Philip Rosenthal、Tanja Schirmeister、Matthias Leippe、Christoph Gelhaus

  DOI：10.3390/molecules14010019

  日期：——

  A series of etacrynic acid derivatives was synthesized and screened for their in vitro activity against Plasmodium falciparum, as well as their activity against recombinantly expressed falcipain-2 and -3. The two most active compounds of the series displayed IC50 values of 9.0 and 18.8 μM against Plasmodia.

  一系列依他尼酸衍生物被合成并筛选其对恶性疟原虫的体外活性，以及它们对重组表达的法西平-2和法西平-3的活性。该系列中活性最强的两种化合物对疟原虫的IC50值分别为9.0和18.8 μM。
• Simple Access to Highly Functional Bicyclic γ- and δ-Lactams: Origins of Chirality Transfer to Contiguous Tertiary/Quaternary Stereocenters Assessed by DFT
  作者：Ronan Le Goff、Arnaud Martel、Morgane Sanselme、Ata Martin Lawson、Adam Daïch、Sébastien Comesse

  DOI：10.1002/chem.201405094

  日期：2015.2.9

  Michael acceptors, which leads efficiently to bicyclic lactams. The process is compatible with unsymmetrical electron‐withdrawing groups on the Michael acceptor, which allows the formation of two contiguous and fully controlled tertiary and quaternary stereocenters. In the case of tetrasubstituted Michael acceptors, two adjacent quaternary stereocenters are formed in good yield. Starting from (R)‐phenylglycinol

  本文描述了通过多米诺法合成多取代的恶唑并吡咯烷酮和哌啶子酮的方法。该方法基于羟基卤代酰胺与迈克尔受体之间的反应，该反应可有效生成双环内酰胺。该过程与迈克尔受体上的不对称吸电子基团兼容，从而可以形成两个连续且完全受控的三级和四级立体中心。在四取代的迈克尔受体的情况下，两个相邻的季立体中心以良好的产率形成。从（R）-苯基甘氨醇衍生的酰胺导致收率高到低且立体选择性高的对映体富集的双环内酰胺的形成，因此大大增加了该策略的范围和兴趣。通过DFT计算研究了手性转移和非对映选择性的起源，并将其归因于反应顺序的最后两个步骤之一中的动力学控制。该选择性取决于迈克尔受体上的取代基和钠阳离子螯合。
• Synthesis of Oxazolidin-4-ones: Domino <i>O</i>-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation
  作者：Abderrahman El Bouakher、Ronan Le Goff、Jordan Tasserie、Jérôme Lhoste、Arnaud Martel、Sébastien Comesse

  DOI：10.1021/acs.orglett.6b00851

  日期：2016.5.20

  An original and rapid domino reaction for access to oxazolidin-4-ones is presented. Simply by heating α-bromoamido alcohol in the presence of KNaCO3 and water with readily prepared Michael acceptors, an unprecedented molecular rearrangement is generated. This new methodology enables the hitherto unreported synthesis of functionalized oxazolidin-4-ones. The process was proved to be compatible with a

  提出了一种原始的快速多米诺骨牌反应来获得恶唑烷丁-4-酮。只需在KNaCO 3和存在下的水与易于制备的Michael受体一起加热α-溴酰胺醇，即可产生前所未有的分子重排。这种新方法使功能性的恶唑烷丁-4-酮迄今未见报道。事实证明，该方法可与多种底物兼容，并具有很高的区域选择性。
• Indole derivatives, processes for their preparation, and their use as
  申请人：Troponwerke GmbH & Co. KG

  公开号：US04513004A1

  公开（公告）日：1985-04-23

  The invention relates to indole derivatives identified herein by Formula (I) and a method for their preparation. Also included in the invention are compositions containing said indoles and methods for their use as antiphlogistic agents.

  本发明涉及由公式（I）所确定的吲哚衍生物及其制备方法。本发明还包括含有该吲哚衍生物的组合物以及将其用作抗炎药物的方法。
• Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2-<i>d</i>][1,4]oxazepin-5(3<i>H</i>)ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence
  作者：Abderrahman El Bouakher、Jordan Tasserie、Ronan Le Goff、Jérôme Lhoste、Arnaud Martel、Sébastien Comesse

  DOI：10.1021/acs.joc.7b00629

  日期：2017.6.2

  proved to be chemo-, regio-, and stereoselective and allows the formation of a large diversity of highly functional 7-membered rings in good yields up to 95%. The complete shift of the regioselectivity of the intermediate enolate from a C–C to a C–O bond formation, contrary to the already known alkylations of such ambident nucleophiles, is mostly triggered by steric effects. The last step of the sequence

  提出了在温和条件下从α-溴酰胺基醇和Michael受体开始合成新的oxazolo [3,2- d ] [1,4] oxazep​​in-5（3 H）-的方法。事实证明，这种多米诺骨牌工艺具有化学选择性，区域选择性和立体选择性，并且可以形成高达95％的高收率的多种多样的高功能7元环。中间烯醇的区域选择性从C–C到C–O键形成的完全转变与这种环境友好的亲核试剂的已知烷基化相反，主要是由空间效应触发的。序列的最后一步是通过DFT建模的，从而给出了该C–C与C–O键移位的一些重要见解。