methyl 2-(methoxyimino)-3-oxopentanoate | 155299-27-7

• 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-oxopentanoate
• 英文别名: Methyl β-keto-α-methoximinovalerate；Methyl 2-methoxyimino-3-oxopentanoate
• CAS: 155299-27-7
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: DIJCRBGBDATKAO-UHFFFAOYSA-N

物化性质

• 沸点：
  218.0±23.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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-oxopentanoate 在 蔗糖 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以24%的产率得到dimethyl 3,6-diethylpyrazine-2,5-dicarboxylate
  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
• 作为产物：
  描述：

  methyl 2-(hydroxyimino)-3-oxopentanoate 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以94%的产率得到methyl 2-(methoxyimino)-3-oxopentanoate
  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

• Heteroaromatic compounds and crop protection agents containing them
  申请人：BASF Aktiengesellschaft

  公开号：US05663185A1

  公开（公告）日：1997-09-02

  Heteroaromatic compounds of the formulae IA and IB ##STR1## where the dashed line is a double bond between the carbon atom and a Z atom, and the index and the substituents have the following meanings: R.sup.1 alkyl, alkoxy, alkylamino R.sup.2 alkyl; A a direct bond; alkylene, alkenylene, alkynylene; O, S, S-oxides, N and alkylene derivatives or oxime radicals thereof B hydrogen, halogen, alkyl, alkenyl, alkynyl; cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl, hetaryl U CH.sub.2, CHCl, CHR.sup.2 or NOR.sup.2 ; X hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, hetaryl; oxi- and thio derivatives thereof, carbonyl derivatives thereof, carbonyloxy derivatives thereof, amino derivatives thereof, oxime derivatives thereof, amino which may bear one or two of the abovementioned groups; m 1 or 2, Y oxygen or sulfur; Z.sup.1 -Z.sup.2, Z.sub.3 -Z.sub.4, together with the carbon atom to which they are bonded, are the radical of a heteroaromatic, and fungicides containing these compounds.

  式IA和IB的杂芳化合物，其中虚线表示碳原子和Z原子之间的双键，指标和取代基具有以下含义：R.sup.1烷基，烷氧基，烷基氨基R.sup.2烷基；A直接键；烷基，烯基，炔基；O，S，S-氧化物，N和烷基衍生物或其氧肟基团B氢，卤素，烷基，烯基，炔基；环烷基，环烯基，环炔基，杂环烷基，芳基，杂芳基U CH.sub.2，CHCl，CHR.sup.2或NOR.sup.2；X氢，氰基，硝基，卤素，烷基，烯基，炔基，环烷基，环烯基，杂环烷基，芳基，杂芳基；其氧和硫衍生物，羰基衍生物，羰氧基衍生物，氨基衍生物，肟衍生物，氨基可能带有上述其中一种或两种基团；m 1或2，Y氧或硫；Z.sup.1 -Z.sup.2，Z.sub.3 -Z.sub.4，与它们结合的碳原子一起，是杂芳基的基团，以及含有这些化合物的杀真菌剂。
• Synthesis of pyrazine via chemoselective reduction of β-keto-α-oximino ester using baker’s yeast
  作者：Kilwoong Mo、Jin Hyeong Park、Soon Bang Kang、Youseung Kim、Yong Sup Lee、Jae Wook Lee、Gyochang Keum

  DOI：10.1016/j.molcatb.2015.11.003

  日期：2016.1

  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.