3-Oxo-2-methoxyiminobuttersaeure | 71754-07-9

• 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: 3-Oxo-2-methoxyiminobuttersaeure
• 英文别名: 2-methoxyimino-3-oxobutyrate；2-Methoxyimino-3-oxobutyric acid；2-methoxyimino-3-oxobutanoic acid
• CAS: 71754-07-9
• 化学式: C₅H₇NO₄
• 分子量: 145.115
• InChiKey: PDMXDQQSMYSAKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Oxo-2-methoxyiminobuttersaeure 、 草酰氯 在 N,N-二甲基甲酰胺 作用下， 以 乙醚 为溶剂， 20.0 ℃ 、359.97 kPa 条件下， 反应 1.5h， 以The 2-methoxyimino-3-oxo-butanoyl chloride, syn isomer, thus obtained的产率得到2-Methoxyimino-3-oxo-butanoyl chloride
  参考文献：
  名称：

  Cephalosporin derivatives

  摘要：

  公式为：##STR1##的新头孢菌素，其中n=0或1，R.sub.1是公式的基团：##STR2## [其中R.sub.4是保护基团，R.sub.5是氢，烷基，乙烯基，氰甲基或保护基团]，或R.sub.1是保护基团，R.sub.2是保护基团或酶可去除的基团，或R.sub.1是酰基基团，可以以不同的方式被取代，R.sub.2是保护基团，如果n=0，则为3-氧乙基-双环辛-2-烯或-双环辛-3-烯或3-氧乙基亚双环辛烷形式，如果n=1，则为3-氧乙基-双环辛-2-烯或3-氧乙基亚双环辛烷形式，可用作制备3-硫基乙烯基头孢菌素的中间体，用作抗菌剂。

  公开号：

  US04365062A1
• 作为产物：
  描述：

  盐酸 、 tert-butyl 2-methoxyimino-3-oxobutyrate 在 二氯甲烷 、 氯化钠 、 magnesium sulfate 作用下， 以 1,4-二氧六环 为溶剂， 反应 13.0h， 以to give 21.8 g of 2-methoxyimino-3-oxobutyric acid的产率得到3-Oxo-2-methoxyiminobuttersaeure
  参考文献：
  名称：

  Method for production of 2-oxyimino-3-oxobutyric acids

  摘要：

  一种有利的方法可以在商业规模上大量生产2-取代氧亚胺基-3-氧代丁酸，这些化合物可用作氨基噻唑头孢菌素合成中间体。该方法的特点是将叔丁基2-取代氧亚胺基-3-氧代丁酸酯与氢卤酸在无水有机溶剂中反应。

  公开号：

  US04927964A1

文献信息

• 3-Thiovinyl-cephalosporins
  申请人：Rhone-Poulenc Industries

  公开号：US04307116A1

  公开（公告）日：1981-12-22

  Novel cephalosporins of the general formula (I); ##STR1## in which R is alkyl, L-2-amino-2-carboxy-ethyl, phenyl, pyridyl, pyridyl-N-oxide, pyrimidin-2-yl, substituted pyridazin-3-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position, 1,3,4-triazol-5-yl or 2-alkoxycarbonyl-1,3,4-triazol-5-yl substituted in the 1-position, 1,4-dialkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 1-alkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 2-alkyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl, triazol-5-yl, 1,3,4-thiadiazol-5-yl which is substituted or unsubstituted, 1,2,4-thiadiazol-5-yl which is substituted, 1,3,4-oxadiazol-5-yl which is substituted or unsubstituted, oxazol-2-yl which is substituted or unsubstituted or tetrazol-5-yl which is substituted or unsubstituted in the 1-position, R' is a hydrogen atom or a radical of the general formula (II); ##STR2## and R.sup.o is hydrogen, alkyl, vinyl or cyanomethyl, as well as their salts, are useful as anti-bacterial agents.

  通式(I)的新型头孢菌素；其中R为烷基，L-2-氨基-2-羧基乙基，苯基，吡啶基，吡啶-N-氧化物，嘧啶-2-基，取代的吡啶-3-基，4-位取代的5,6-二氧化-1,4,5,6-四氢-1,2,4-三嗪-3-基，1,3,4-三唑-5-基或1-位取代的2-烷氧羰基-1,3,4-三唑-5-基，1,4-二烷基-5,6-二氧化-1,4,5,6-四氢-1,2,4-三嗪-3-基，1-烷基-5,6-二氧化-1,4,5,6-四氢-1,2,4-三嗪-3-基，2-烷基-5,6-二氧化-1,2,5,6-四氢-1,2,4-三嗪-3-基，三唑-5-基，1,3,4-噻二唑-5-基，取代或未取代的1,2,4-噻二唑-5-基，取代或未取代的1,3,4-噁二唑-5-基，取代或未取代的噁唑-2-基或取代或未取代的1-位四唑-5-基，R'为氢原子或通式(II)的基团；其中R.sup.o为氢，烷基，乙烯基或氰甲基，以及它们的盐，可用作抗菌剂。
• 3-Vinyl-cephalosporins
  申请人：Rhone-Poulenc Industries

  公开号：US04307230A1

  公开（公告）日：1981-12-22

  Novel 3-vinyl-cephalosporins of the formula ##STR1## in which n is 0 or 1, R.sub.1 is hydrogen, a radical of the formula ##STR2## [in which R.sub.4 is hydrogen or a protective radical and R.sub.5 is hydrogen, alkyl, vinyl or cyanomethyl or is a protective radical], or a protective radical, and R.sub.2 is hydrogen, a protective radical or an enzymatically removable radical, or R.sub.1 is hydrogen or an acyl radical which may carry various substituents and R.sub.2 is hydrogen or a protective radical, and R.sub.3 is a radical of the general formula R'.sub.3 --SO.sub.2 --O-- or R".sub.3 --CO--O--, in which R'.sub.3 is alkyl, trifluoromethyl, trichloromethyl or phenyl which is substituted by a halogen atom or by an alkyl or nitro radical, and R".sub.3 is defined like R'.sub.3 or represents methyl which is substituted by acyl or alkoxycarbonyl, or represents ethyl or propyl substituted in the 2-position by acyl or alkoxycarbonyl. These compounds are useful as intermediates for the preparation of antibiotic 3-thiovinyl-cephalosporins.

  式为##STR1##的新型3-乙烯基头孢菌素，其中n为0或1，R.sub.1为氢，式为##STR2##的基团[其中R.sub.4为氢或保护基团，R.sub.5为氢、烷基、乙烯基或氰甲基或为保护基团]，或保护基团，R.sub.2为氢、保护基团或酶可去除的基团，或R.sub.1为氢或可携带各种取代基的酰基基团，R.sub.2为氢或保护基团，R.sub.3为一般式R'.sub.3--SO.sub.2--O--或R".sub.3--CO--O--的基团，其中R'.sub.3为烷基、三氟甲基、三氯甲基或被卤素原子、烷基或硝基基团取代的苯基，R".sub.3的定义与R'.sub.3相同或代表被酰基或烷氧羰基取代的甲基，或代表2-位被酰基或烷氧羰基取代的乙基或丙基。这些化合物可用作制备抗生素3-硫代乙烯基头孢菌素的中间体。
• 3-Vinyl-cephalosporin derivatives
  申请人：Rhone-Poulenc Industries

  公开号：US04307233A1

  公开（公告）日：1981-12-22

  Novel 3-vinyl-cephalosporin derivates of the general formula ##STR1## in the bicyclooct-2-ene or bicyclooct-3-ene form, in which R.sub.1 is a protective radical or is a radical of the general formula ##STR2## in which R.sub.5 is hydrogen, alkyl, vinyl or cyanomethyl, or a protective radical, and R.sub.6 is hydrogen or a protective radical, and R.sub.2 is a protective radical or an enzymatically removable radical, or R.sub.1 is an acyl radical, which may carry various substituents, and R.sub.2 represents a protective radical, and R.sub.3 and R.sub.4, which are identical or different, represent alkyl (optionally substituted by hydroxyl, alkoxy, amino, alkylamino or dialkylamino) or phenyl, or form, together with the nitrogen atom, a saturated 5-membered or 6-membered heterocyclic ring optionally containing another hetero-atom, their E- and Z-forms and their mixtures, are useful as intermediates for the preparation of 3-thiovinyl cephalosporins useful as antibacterial agents.

  通式为##STR1##的新型3-乙烯基头孢菌素衍生物，以双环辛二烯或双环辛三烯的形式存在。其中，R.sub.1是保护基或通式##STR2##的基团，其中R.sub.5是氢、烷基、乙烯基或氰甲基，或保护基；R.sub.6是氢或保护基；R.sub.2是保护基或酶可去除的基团；或R.sub.1是酰基基团，可携带各种取代基；R.sub.2代表保护基；R.sub.3和R.sub.4相同或不同，代表烷基（可选地被羟基、烷氧基、氨基、烷基氨基或二烷基氨基取代）或苯基，或与氮原子一起形成饱和的5元环或6元环杂环，可选地含有另一个杂原子。它们的E和Z形式及其混合物，可用作制备3-硫代乙烯基头孢菌素的中间体，用于制备抗菌剂。
• 4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04845257A1

  公开（公告）日：1989-07-04

  A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.

  一种制备4-卤代-2-(取代或未取代)羟基亚胺-3-酮丁酸酯或酰胺的方法，该方法是制备含有氨基噻唑基团头孢菌素的合成中间体，其特征在于将2-(取代或未取代)羟基亚胺-3-酮丁酸或其酯或酰胺与硅烷化试剂反应，并将所得的新型2-(取代)羟基亚胺-3-硅氧基-3-丁烯酸酯或酰胺与卤代试剂反应。
• Method for production of 2-oxyimino-3-oxobutyric acids
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04927964A1

  公开（公告）日：1990-05-22

  An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.

  一种有利的方法可以在商业规模上大量生产2-取代氧亚胺基-3-氧代丁酸，这些化合物可用作氨基噻唑头孢菌素合成中间体。该方法的特点是将叔丁基2-取代氧亚胺基-3-氧代丁酸酯与氢卤酸在无水有机溶剂中反应。