methyl 2-(methoxyimino)-3-oxobutanoate | 65243-07-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2-(methoxyimino)-3-oxobutanoate
• 英文别名: methyl 2-methoxyimino-3-oxobutanoate；2-(methoxyimino)-3-oxo-butanoic acid, methyl ester
• CAS: 65243-07-4
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: MGXLNEQONXBEIA-UHFFFAOYSA-N

物化性质

• 沸点：
  198.0±23.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(methoxyimino)-3-oxobutanoate 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以86%的产率得到methyl 2,3-dioxobutanoate
  参考文献：
  名称：

  Zinc-Induced Deoximation of α,α′-Dioxo-Type Oximes and Oxime Ethers Leading to α,β-Diketo Esters

  摘要：

  在温和条件下，使用锌/乙酸完成了多种α,α′-二酮型肟和肟醚的去氧化反应，获得了良好产率的α,β-二酮酯。

  DOI：

  10.1246/bcsj.77.1407
• 作为产物：
  描述：

  methyl 3-oxo-2-oximinobutanoate 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以92%的产率得到methyl 2-(methoxyimino)-3-oxobutanoate
  参考文献：
  名称：

  Synthesis of pyrazine via chemoselective reduction of β-keto-α-oximino ester using baker’s yeast

  摘要：

  The synthesis of pyrazines by the baker's yeast-mediated reaction of beta-keto-alpha-oximino esters and amides is described. Baker's yeast reduced oximes selectively over ketones of beta-keto-alpha-oximino esters to give the corresponding beta-keto-alpha-amino ester intermediates, which underwent spontaneous dimerization followed by air-induced aromatization to yield pyrazines. The chemoselective reduction of beta-keto-alpha-oximino amides using baker's yeast also afforded the corresponding pyrazines. Interestingly, both hydroximes and alkoximes gave the pyrazines by the baker's yeast-mediated reduction via the corresponding amino ketones, the known precursors of pyrazines. The reaction was strongly dependent upon pH of reaction medium, and gave optimum yields at pH 5. These results demonstrate that pyrazines were synthesized efficiently and eco-friendly using a whole-cell biocatalytic system as an alternative to chemical reduction. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.11.003

文献信息

• Cepham compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04379922A1

  公开（公告）日：1983-04-12

  This invention relates to new compounds comprising alkoxyimino dioxy butyric acid cepham derivatives, useful as intermediates in the production of antimicrobial agents.

  本发明涉及新的化合物，包括烷氧基亚亚硝基丁酸头孢衍生物，在生产抗微生物药物的中间体中有用。
• Cephalosporin derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04380541A1

  公开（公告）日：1983-04-19

  Novel 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporanic acid derivatives of the formula: ##STR1## wherein R.sup.1 NH is an amino group which may optionally be protected, R.sup.2 is a halogen atom or a hydroxyl, thiol or amino group which may optionally be substituted; COOR is a carboxyl group which may optionally be esterified, and pharmaceutically acceptable salts thereof, have excellent antimicrobial activity against a broad spectrum of microorganisms including Gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae, Citrobacter freundii. Thus, these compounds may be used as antibacterial agents for therapeutic purposes.

  7-[2-(2-氨基噻唑-4-基)-2-(syn)-甲氧基亚胺基乙酰胺基]头孢菌素酸衍生物的化学式为：##STR1## 其中，R.sup.1 NH是一种氨基基团，可以选择性地被保护，R.sup.2是卤素原子或羟基、硫醇或氨基基团，可以选择性地被取代；COOR是一种羧基团，可以选择性地被酯化，以及其药学上可接受的盐，对广谱微生物包括革兰氏阴性菌如大肠杆菌、马赛氏菌、雷特格氏变形杆菌、克雷伯氏菌具有优异的抗微生物活性。因此，这些化合物可以用作治疗用的抗菌剂。
• Esters of
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04680390A1

  公开（公告）日：1987-07-14

  The compounds are of the class of esters of 7-[2-(2-aminothiazol-4-yl-)-2-(syn)methoxyiminoacetamido] cephalosporin derivatives, including lower alkoxymethyl, .alpha.-lower alkoxy-.alpha.-substituted methyl, lower alkylthiomethyl, acyloxymethyl, ethoxycarbonyloxy-1-methylmethyl and .alpha.- acyloxy-.alpha.-substituted methyl esters. The compounds are useful against a broad spectrum of bacteria, particularly gram-negative bacteria, and may be administered in the form of injections, capsules, tablets and granules.

  这些化合物属于7-[2-(2-氨基噻唑-4-基)-2-(syn)甲氧基亚胺基]头孢菌素衍生物的酯类，包括较低的烷氧甲基、α-较低烷氧基-α-取代甲基、较低烷基硫甲基、酰氧甲基、乙氧羰基氧-1-甲基甲基和α-酰氧基-α-取代甲基酯。这些化合物对广谱细菌，特别是革兰氏阴性菌有用，并可以以注射、胶囊、片剂和颗粒的形式给予。
• [3-Heterocyclic-7-(2-methoxyimino-2-aminothiazolyl)
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04197298A1

  公开（公告）日：1980-04-08

  7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporanic acid derivatives of the formula; ##STR1## wherein R.sup.1 NH is an amino group which may optionally be protected; COOR.sup.2 is a carboxyl group which may optionally be esterified; X is oxygen, sulfur or an imino group which may optionally be substituted; B is hydrogen or a hydroxyl, amino, thiol or hydrocarbon group which may optionally be substituted, or a salt thereof, are novel, .beta.-lactamase-resistant and low-toxicity compounds which display excellent activity against a broad spectrum of microorganisms including Gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae, Citrobacter freundii. Thus, these compounds can be used for antibacterial agents in therapeutical purpose.

  本发明涉及一种7-[2-(2-氨基噻唑-4-基)-2-(syn)-甲氧基亚胺基]头孢菌素酸衍生物，其化学式为：##STR1##其中，R.sup.1 NH为氨基，可以选择性地被保护；COOR.sup.2为羧基，可以选择性地被酯化；X为氧、硫或亚胺基，可以选择性地被取代；B为氢或羟基、氨基、硫醇或碳氢基团，可以选择性地被取代，或其盐。这些新颖的β-内酰胺酶抗性和低毒性化合物对包括大肠杆菌、马赛氏菌、雷特格氏变形杆菌、克雷伯氏菌、弗氏柠檬酸杆菌在内的广谱微生物表现出出色的活性。因此，这些化合物可以作为治疗用抗菌剂。
• 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporin
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04510138A1

  公开（公告）日：1985-04-09

  An antibacterial composition is provided consisting of a 7-[2-(2-aminothiazol)-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporin compound of the formula ##STR1## wherein R.sub.2 NH is amino or a protected amino group, n is an integer of 1 to 3 and R is a di-C.sub.1-3 alkylamino, carboxyl or sulfo group, or a pharmaceutically acceptable salt or ester thereof.

  提供了一种抗菌组合物，由公式 ##STR1## 中的 7-[2-(2-氨基噻唑-4-基)-2-(syn)-甲氧基亚胺基乙酰氨基]头孢菌素化合物组成，其中 R.sub.2 NH 是氨基或受保护的氨基基团，n 是1至3的整数，R 是二级C.sub.1-3烷基氨基，羧基或磺酸基，或其药学上可接受的盐或酯。