tert-butyl 2-(methoxy(methyl)amino)-2-oxo-1-phenylethylcarbamate | 147353-99-9

• 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-(methoxy(methyl)amino)-2-oxo-1-phenylethylcarbamate
• 英文别名: tert-butyl N-[2-[methoxy(methyl)amino]-2-oxo-1-phenylethyl]carbamate
• CAS: 147353-99-9
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: YSHFHFQXCUVLDX-UHFFFAOYSA-N

物化性质

• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(methoxy(methyl)amino)-2-oxo-1-phenylethylcarbamate 在 盐酸 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 5.03h， 生成 5-(4-hexylphenyl)-4-phenyl-1H-imidazol-2-amine;hydrochloride
  参考文献：
  名称：

  基于2-氨基咪唑支架的抗分枝杆菌生物膜剂的鉴定。

  摘要：

  结核病（TB）仍然是全球性的重大健康问题，因此迫切需要新的治疗方法。病原体结核分枝杆菌驻留在宿主巨噬细胞内并形成生物膜样群落的能力有助于该疾病的持久性和药物耐受性。可以预防或逆转生物膜样表型的化合物有可能与结核病抗生素一起使用，以克服这种耐受性并缩短治疗时间。我们使用耻垢分枝杆菌作为替代生物，报告了两种抑制和分散分枝杆菌生物膜的新的2-氨基咪唑化合物的鉴定，它们与异烟肼和利福平协同作用，可在体外根除预先形成的耻垢分枝杆菌生物膜，对马勒菌无毒，并展示小鼠血浆中的稳定性。

  DOI：

  10.1002/cmdc.201900033
• 作为产物：
  描述：

  N-Boc-DL-苯基甘氨酸 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 2-(methoxy(methyl)amino)-2-oxo-1-phenylethylcarbamate
  参考文献：
  名称：

  Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit

  摘要：

  Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and alpha-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 mu M. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 mu M. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.021

文献信息

• Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation
  作者：Chenhao Zhang、Anthony Z. Gao、Xin Nie、Chen-Xi Ye、Sergei I. Ivlev、Shuming Chen、Eric Meggers

  DOI：10.1021/jacs.1c06637

  日期：2021.8.25

  deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic

  该研究报告了在单个反应中通过去质子化，然后对映选择性质子化，在 α 位带有立体中心的酮的催化去外消旋化。先前使该策略难以捉摸的微观可逆性原理被通过单电子转移和随后的氢原子转移 (HAT) 进行的光氧化还原去质子化所克服。具体而言，在单一光催化剂和叔胺存在下外消旋吡啶基酮的辐照可提供对映体过量高达 97% 的非外消旋羰基化合物。光催化剂收集可见光，诱导氧化还原过程，并负责不对称诱导，而胺作为单电子供体、HAT 试剂和质子源。
• Asymmetric Imino Aza-enamine Reaction Catalyzed by Axially Chiral Dicarboxylic Acid: Use of Arylaldehyde <i>N</i>,<i>N</i>-Dialkylhydrazones as Acyl Anion Equivalent
  作者：Takuya Hashimoto、Maya Hirose、Keiji Maruoka

  DOI：10.1021/ja802704j

  日期：2008.6.18

  Synthetic utility of arylaldehyde N,N-dialkylhydrazones as a practical acyl anion equivalent could be exploited for the first time in the asymmetric imino aza-enamine reaction catalyzed by axially chiral carboxylic acid.

  在轴向手性羧酸催化的不对称亚氨基氮杂-烯胺反应中，首次利用芳醛N,N-二烷基腙作为实用的酰基阴离子等价物的合成效用。
• Small Molecule Suppression of Carbapenem Resistance in NDM-1 Producing <i>Klebsiella pneumoniae</i>
  作者：Roberta J. Worthington、Cynthia A. Bunders、Catherine S. Reed、Christian Melander

  DOI：10.1021/ml200290p

  日期：2012.5.10

  The already considerable global public health threat of multidrug-resistant Gram-negative bacteria has become even more of a concern following the emergence of New Delhi metallo-beta-lactamase (NDM-1) producing strains of Klebsiella pneumoniae and other Gram-negative bacteria. As an alternative approach to the traditional development of new bactericidal entities, we have identified a 2-aminoimidazole-derived small molecule that acts as an antibiotic adjuvant and is able to suppress resistance of a NDM-1 producing strain of K. pneumoniae to imipenem and meropenem, in addition to suppressing resistance of other beta-lactam nonsusceptible K. pneumoniae strains. The small molecule is able to lower carbapenem minimum inhibitory concentrations by up to 16-fold, while exhibiting little bactericidal activity itself.
• Identification of Anti‐Mycobacterial Biofilm Agents Based on the 2‐Aminoimidazole Scaffold
  作者：T. Vu Nguyen、Bradley M. Minrovic、Roberta J. Melander、Christian Melander

  DOI：10.1002/cmdc.201900033

  日期：2019.5.6

  and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.

  结核病（TB）仍然是全球性的重大健康问题，因此迫切需要新的治疗方法。病原体结核分枝杆菌驻留在宿主巨噬细胞内并形成生物膜样群落的能力有助于该疾病的持久性和药物耐受性。可以预防或逆转生物膜样表型的化合物有可能与结核病抗生素一起使用，以克服这种耐受性并缩短治疗时间。我们使用耻垢分枝杆菌作为替代生物，报告了两种抑制和分散分枝杆菌生物膜的新的2-氨基咪唑化合物的鉴定，它们与异烟肼和利福平协同作用，可在体外根除预先形成的耻垢分枝杆菌生物膜，对马勒菌无毒，并展示小鼠血浆中的稳定性。
• Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit
  作者：Megan E. Bolitho、Lark J. Perez、Matthew J. Koch、Wai-Leung Ng、Bonnie L. Bassler、Martin F. Semmelhack

  DOI：10.1016/j.bmc.2011.09.021

  日期：2011.11

  Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and alpha-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 mu M. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 mu M. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen. (C) 2011 Elsevier Ltd. All rights reserved.