benzyl 2-acetamido-3-oxobutanoate | 124576-56-3

• 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: benzyl 2-acetamido-3-oxobutanoate
• CAS: 124576-56-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: GUABYMIBNFXJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3-oxobutanoate 在 palladium 10% on activated carbon 、 氢气 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2,5-二甲基-1,3-恶唑-4-甲酸
  参考文献：
  名称：

  [EN] POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS
  [FR] ANALOGUES DE LA POLYMYXINE UTILES EN TANT QUE POTENTIALISATEURS D'ANTIBIOTIQUE

  摘要：

  该披露提供了式(I)的化合物或其互变异构体，或者上述任一化合物的药学上可接受的盐。变量A、R1和R2在披露中有定义。该披露还包括包含式I化合物和至少一种药学上可接受的载体的药物组合物。该披露还包括一种使细菌对抗菌剂产生敏感的方法，包括向感染有该细菌的患者同时或顺序地给予抗菌剂和式(I)化合物的治疗有效量。

  公开号：

  WO2017189866A1
• 作为产物：
  描述：

  乙酰丙酮苄酯 在 溶剂黄146 、 锌 、 sodium nitrite 作用下， 反应 4.0h， 生成 benzyl 2-acetamido-3-oxobutanoate
  参考文献：
  名称：

  [EN] POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS
  [FR] ANALOGUES DE LA POLYMYXINE UTILES EN TANT QUE POTENTIALISATEURS D'ANTIBIOTIQUE

  摘要：

  该披露提供了式(I)的化合物或其互变异构体，或者上述任一化合物的药学上可接受的盐。变量A、R1和R2在披露中有定义。该披露还包括包含式I化合物和至少一种药学上可接受的载体的药物组合物。该披露还包括一种使细菌对抗菌剂产生敏感的方法，包括向感染有该细菌的患者同时或顺序地给予抗菌剂和式(I)化合物的治疗有效量。

  公开号：

  WO2017189866A1

文献信息

• Catalytic process for preparing optically active threonine
  申请人：Takasago International Corporation

  公开号：EP0322236A2

  公开（公告）日：1989-06-28

  A 2-N-acylaminoacetoacetic ester represented by the formula: wherein R1 represents lower alkyl, or phenyl or benzyl each of which may be substituted with lower alkyl group or lower alkoxy; R2 represents hydrogen, a lower alkyl, lower alkoxy, or phenyl or benzyloxy, each of which may be substituted with lower alkyl or lower alkoxy, is dissolved in a solvent (e.g. an alkanol), mixed with a ruthenium-optically active phosphine complex as a catalyst, and hydrogenated at 25 to 50°C at a H2 pressure of 10-100 kg/cm2 for 15 to 48 hours, to obtain as an intermediate an optically active N-acyl threonine represented by: wherein R1 and R2 are as defined above. The intermediate (II) can be selectively prepared in a high yield and is then hydrolysed with HCI to obtain optically active threonine (CH3CHOHCHNH2COOH). Natural or non-natural type threonine can be prepared selectively by seleoting the absolute configuration of the ligand of the ruthenium-optically active phosphine complex, of which four general formulae are given, all containing a "BINAP" tertiary phosphine; syntheses of the catalyst are given.

  一种 2-N-酰氨基乙酰乙酸酯，由式表示： 其中 R1 代表低级烷基，或苯基或苄基，它们各自可被低级烷基或低级烷氧基取代； R2 代表氢、低级烷基、低级烷氧基或苯基或苄氧基，它们各自可被低级烷基或低级烷氧基取代。例如烷醇）中，与作为催化剂的钌-光学活性膦络合物混合，并在 25 至 50℃、10-100 kg/cm2 的 H2 压力下氢化 15 至 48 小时，以获得光学活性 N-酰基苏氨酸作为中间体： 其中 R1 和 R2 如上定义。 中间体（II）可以选择性地以高产率制备，然后用 HCI 进行水解，得到光学活性苏氨酸（CH3CHOHCHNH2COOH）。通过选择钌-光学活性膦配合物配体的绝对构型，可以选择性地制备天然或非天然苏氨酸，其中给出了四个通式，均含有 "BINAP "叔膦，并给出了催化剂的合成方法。
• Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide
  作者：Tetsuhiro Nemoto、Teisuke Harada、Takayoshi Matsumoto、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2007.07.020

  日期：2007.9

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.
• Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
  作者：Juan F. Sanz-Cervera、Raül Blasco、Julio Piera、Michael Cynamon、Ignacio Ibáñez、Marcelo Murguía、Santos Fustero

  DOI：10.1021/jo9016265

  日期：2009.12.4

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.
• US4906773A
  申请人：——

  公开号：US4906773A

  公开（公告）日：1990-03-06
• [EN] POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS<br/>[FR] ANALOGUES DE LA POLYMYXINE UTILES EN TANT QUE POTENTIALISATEURS D'ANTIBIOTIQUE
  申请人：SPERO OPCO

  公开号：WO2017189866A1

  公开（公告）日：2017-11-02

  The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

  该披露提供了式(I)的化合物或其互变异构体，或者上述任一化合物的药学上可接受的盐。变量A、R1和R2在披露中有定义。该披露还包括包含式I化合物和至少一种药学上可接受的载体的药物组合物。该披露还包括一种使细菌对抗菌剂产生敏感的方法，包括向感染有该细菌的患者同时或顺序地给予抗菌剂和式(I)化合物的治疗有效量。