tert-butyl (2-oxo-2-(phenylamino)ethyl)carbamate | 27904-92-3

• 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: tert-butyl (2-oxo-2-(phenylamino)ethyl)carbamate
• 英文别名: Tert-butyl n-[(phenylcarbamoyl)methyl]carbamate；tert-butyl N-(2-anilino-2-oxoethyl)carbamate
• CAS: 27904-92-3
• 化学式: C₁₃H₁₈N₂O₃
• mdl: MFCD10043451
• 分子量: 250.298
• InChiKey: SXMVQSMVZIZWDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-oxo-2-(phenylamino)ethyl)carbamate 在 三氟乙酸 作用下， 以97 %的产率得到2-氨基-N-苯基乙酰胺
  参考文献：
  名称：

  作为高效几丁质酶抑制剂的芳香族 2-(3-(甲基氨基甲酰基) 胍基)-N-酰基乙酰胺的发现

  摘要：

  几丁质酶是重要的糖苷水解酶，与细菌发病机制、真菌细胞壁重塑和昆虫蜕皮密切相关。因此，几丁质酶已成为治疗药物和杀虫剂的有吸引力的目标。在本研究中，我们基于天然产物argifin的N-甲基氨基甲酰基胍基设计并合成了一系列新型几丁质酶抑制剂。活性最强的化合物8h对 I 组几丁质酶Hs Chit1、Sm ChiB 和Of Chi-h 表现出强烈的抑制活性，IC 50值分别为 0.19 µM、4.2 nM 和 25 nM。结合模式研究表明化合物8h在几丁质酶的 +1 或 +2 亚位点形成 π-π 堆积/疏水相互作用。此外，在药效团N-甲基氨基甲酰基胍基和 -1 亚位点的关键残基之间形成关键氢键网。总之，这项研究的结果为使用平面结构和N-甲基氨基甲酰基胍基的组合开发有效的小分子几丁质酶抑制剂提供了新的见解。

  DOI：

  10.1016/j.bmc.2023.117172
• 作为产物：
  描述：

  2-(hydroxyimino)-4-methyl-3-oxo-N-phenylpentanamide 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.5h， 生成 tert-butyl (2-oxo-2-(phenylamino)ethyl)carbamate
  参考文献：
  名称：

  4,5-Dioxo-imidazolinium Cation Activation of 1-Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione

  摘要：

  Cyanoformamides are prevalent as versatile building blocks for accessing synthetically useful intermediates and biologically active compounds. The development of a milder, simpler, and more efficient approach to cyanoformamides is nontrivial. Herein, we demonstrate the effectiveness of 4,S-dioxo-imidazolinium cation activation for transforming 1-aryl-1-carbamoyl oximes to cyanoformamides. By making use of the readily available and highly modifiable dichloroimidazolidinediones (DCIDs), this novel method of activation offers reactivity remarkably greater than that of other reported protocols, exhibits a high functional group compatibility with mild conditions, and could be scaled up easily. More than 30 examples are demonstrated with good to excellent yields in short reaction times. This research not only provides a mild and efficient alternative approach to assembling a portfolio of cyanoformamides but also extends the dichloroimidazolidinedione-mediated chemistry to encompass the C-C bond cleavage reaction.

  DOI：

  10.1021/acs.joc.9b02992

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• New isoleucine derived dipeptides as antiprotozoal agent: Synthesis, in silico and in vivo studies.
  作者：Ogechi C. Ekoh、Uchechukwu C. Okoro、Rafat Ali、David I. Ugwu、Sunday N. Okafor、James A. Ezugwu

  DOI：10.1016/j.molstruc.2021.130017

  日期：2021.5

  aceturate. In the antimalarial study, 11b was the most active compound, even better than the standard. Molecular docking result suggests good interaction between the reported compounds and the target protein. The results of haematological analysis, liver and kidney function tests showed that the compounds had no adverse effect on the blood and organs. Compound 11b stands out among the derivatives haven shown

  疟疾耐药性寄生虫的出现越来越多，锥虫病的有效化学疗法不足，代表了热带地区传染病治疗的巨大挑战。关于开发有效的抗原生动物剂，通过使用肽偶联剂将化合物（10）与（8a-j）缩合，合成了十种新的甘草二肽磺酰胺衍生物。化合物11b，11i和11j最能清除11b小鼠的锥虫布氏锥虫，并具有与醋酸二米那嗪相当的活性。在抗疟疾研究中，11b是活性最高的化合物，甚至优于标准化合物。分子对接结果表明所报道的化合物与靶蛋白之间具有良好的相互作用。血液学分析，肝和肾功能测试的结果表明该化合物对血液和器官没有不良影响。化合物11b在衍生物中脱颖而出，这些衍生物在抗疟和抗锥虫试验中均显示出更好的活性。
• Design, synthesis and preliminary bioactivity evaluations of 8-hydroxyquinoline derivatives as matrix metalloproteinase (MMP) inhibitors
  作者：Chen Chen、Xinying Yang、Hao Fang、Xuben Hou

  DOI：10.1016/j.ejmech.2019.111563

  日期：2019.11

  Matrix metalloproteinases (MMPs) play important roles in many diseases including cancer. With moderate metal-binding affinity, 8-hydroxyquinoline has gained much interest in current drug design and development. Specially, it has been reported that 8-hydroxyquinoline derivatives serve as MMP-2 inhibitors with micromolar IC50 values. In the current study, a series of 8-hydroxyquinoline derivatives were

  基质金属蛋白酶（MMP）在包括癌症在内的许多疾病中都起着重要作用。具有适度的金属结合亲和力，8-羟基喹啉在当前的药物设计和开发中引起了很多兴趣。特别地，已经报道8-羟基喹啉衍生物用作具有微摩尔IC 50值的MMP-2抑制剂。在当前的研究中，设计并合成了一系列8-羟基喹啉衍生物，作为新的MMP-2和MMP-9抑制剂。活性最强的化合物5e和5h不仅对亚微摩尔水平的IC 50表现出对MMP-2 / 9的良好抑制活性，而且在A549细胞系中具有强大的抗增殖，抗侵袭和抗血管生成活性。免疫印迹也显示5e和5h下调A549细胞系中MMP-2和MMP-9的表达。此外，流式细胞术分析表明化合物5e可以促进A549细胞的体外凋亡。分子对接分析还揭示了MMP-2和MMP-9活性位点中5e的有利结合模式。
• CATALYST FOR ASYMMETRIC HYDROGENATION AND METHOD FOR MANUFACTURING OPTICALLY ACTIVE CARBONYL COMPOUND USING THE SAME
  申请人：YAMADA Shinya

  公开号：US20120136176A1

  公开（公告）日：2012-05-31

  The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

  本发明提供了一种用于通过选择性不对称加氢α，β-不饱和羰基化合物制备光学活性羰基化合物的催化剂，该催化剂在反应混合物中不溶解，并提供了制备相应光学活性羰基化合物的方法。特别地，该发明提供了一种催化剂，通过选择性不对称加氢柠檬醛、香叶醛或柠檬醛制备出用作香料或芳香剂的光学活性香茅醛。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，包括：来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种金属负载物质，其中至少一种金属负载在一种载体上；一种光学活性肽化合物；和一种酸，还涉及使用该催化剂制备光学活性羰基化合物的方法。
• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。