(E)-2-(methoxyimino)-2-phenylacetic acid | 39684-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(methoxyimino)-2-phenylacetic acid
• 英文别名: α-methoxyiminophenylacetic acid；syn-2-methoxyimino-2-phenylacetic acid；(Z)-2-(methoxyimino)-2-phenylacetic acid；(2E)-2-methoxyimino-2-phenylacetic acid
• CAS: 39684-46-3
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: ISFFCSPHFNWPST-CSKARUKUSA-N

物化性质

• 沸点：
  306.7±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(methoxyimino)-2-phenylacetic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3
• 作为产物：
  描述：

  L-苯甘氨酸 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 (E)-2-(methoxyimino)-2-phenylacetic acid
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3

文献信息

• Efficient synthesis of (Z)- and (E)-methyl 2-(methoxyimino)-2-phenylacetate
  作者：Yong-Jin Wu、Stella Huang、Alicia Ng、Qi Gao、S. Roy Kimura、David R. Langley

  DOI：10.1016/j.tetlet.2010.02.073

  日期：2010.4

  2-oxo-2-phenylacetate (3) gave the (Z)-methyl 2-(methoxyimino)-2-phenylacetate (1) in 71% yield, while the E oxime 2 was prepared from 3 in 65% yield via oxime isomerization of 2-(methoxyimino)-2-phenylacetic acid (5). Computational studies suggest that the isomerization of 5 is thermodynamically driven, while the direct oximation of ketoester 3 is kinetically controlled.

  将2-氧代-2-苯基乙酸酯（3）直接肟化，得到（Z）-2-（甲氧基亚氨基）-2-苯基乙酸甲酯（1），产率为71％，而由3的E-肟2的产率为65％。通过2-（甲氧基亚氨基）-2-苯基乙酸的肟异构化（5）。计算研究表明，5的异构化是热力学驱动的，而酮酸酯3的直接肟化是动力学控制的。
• 13-substituted milbemycin derivatives, their preparation and their use
  申请人：Sankyo Company, Limited

  公开号：US05614470A1

  公开（公告）日：1997-03-25

  13-Substituted milbemycin derivatives having the formula (I): ##STR1## wherein: R.sup.1 is methyl, ethyl, isopropyl or sec-butyl; R.sup.2 is hydrogen or alkyl; X is (.alpha.-hydroxyimino- or .alpha.-alkoxyimino-substituted)-arylmethyl or (.alpha.-hydroxyimino- or .alpha.-alkoxyimino-substituted)-heterocyclylmethyl, N-substituted-aminophenyl or N-substituted-aminophenoxy; m is 0 or 1; and n is 0 or 1; are valuable as agricultural and horticultural anthelmintic, acaricidal and insecticidal agents.

  具有以下结构式（I）的13-取代的米尔贝霉素衍生物：其中：R.sup.1为甲基、乙基、异丙基或仲丁基；R.sup.2为氢或烷基；X为(.alpha.-羟氧亚胺基或.alpha.-烷氧亚胺基取代)-芳基甲基或(.alpha.-羟氧亚胺基或.alpha.-烷氧亚胺基取代)-杂环甲基、N-取代氨基苯基或N-取代氨基苯氧基；m为0或1；n为0或1；在农业和园艺上作为抗蠕虫、杀螨和杀虫剂具有价值。
• Thioether derivatives as protein kinase inhibitors
  申请人：KTB Tumorforschungsgesellschaft mbH

  公开号：EP2733146A1

  公开（公告）日：2014-05-21

  The present invention relates to thioether derivatives as protein kinase inhibitors, which are useful for the treatment, relieve and/or prevention of diseases associated with abnormal and hyperproliferation of cells in a mammal, especially humans, and which are particularly useful for the treatment of all forms of cancer.

  本发明涉及硫醚衍生物作为蛋白激酶抑制剂，其对于哺乳动物，尤其是人类中细胞异常和过度增殖所致的疾病的治疗、缓解和/或预防非常有用，特别适用于治疗所有形式的癌症。
• Penicillins having a 6.beta.-(.alpha.-etherified oximino) acylamido group
  申请人：Glaxo Laboratories Limited

  公开号：US03932385A1

  公开（公告）日：1976-01-13

  The invention provides novel antibiotic compounds which are 6.beta.-acylamidopenam-3-carboxylic acids, and non-toxic derivatives thereof, characterized in that the acylamido group has the structure ##EQU1## WHERE R is a hydrogen atom or an organic group and R.sup.a is an etherifying monovalent organic group linked to the oxygen atom through a carbon atom. The compounds may be either syn or anti isomers or may exist as mixtures e.g. containing at least 75 percent of one isomer. These antibiotic compounds possess high antibacterial activity against a range of gram positive organisms including penicillinase - producing staphylococci coupled with high activity against strains of the gram-negative organism Haemophilus influenzae. The invention is also concerned with the administration of the compounds.

  本发明提供了新型抗生素化合物，其为6.beta.-酰胺基青霉烷-3-羧酸，以及其非毒性衍生物，其特征在于酰胺基具有以下结构## EQU1 ##其中R是氢原子或有机基团，而R.sup.a是通过碳原子与氧原子连接的醚化一价有机基团。这些化合物可以是同构体或反异构体，也可以存在混合物，例如含有至少75％的一个异构体。这些抗生素化合物对一系列革兰氏阳性菌具有高度的抗菌活性，包括产青霉素酶的葡萄球菌，并且对革兰氏阴性菌流感嗜血杆菌的菌株也具有高度的活性。本发明还涉及该化合物的给药。
• [EN] INGENOL-3-ACYLATES I<br/>[FR] INGÉNOL-3-ACYLATES I
  申请人：LEO PHARMA AS

  公开号：WO2012085189A1

  公开（公告）日：2012-06-28

  The invention relates to compounds of general formula (I) wherein R is (C1-C7)alkyl, (C2-C7)alkenyl or (C2-C7)alkynyl; wherein R is substituted with R1; and pharmaceutically acceptable salts, hydrates, or solvates thereof, for use -alone or in combination with one or more other pharmaceutically active compounds- in therapy, for preventing, treating or ameliorating diseases or conditions responsive to stimulation of neutrophil oxidative burst, responsive to stimulation of keratinocyte IL-8 release or responsive to induction of necrosis.

  本发明涉及一般式(I)的化合物，其中R为(C1-C7)烷基，(C2-C7)烯基或(C2-C7)炔基；其中R被R1取代；以及其药学上可接受的盐、水合物或溶剂化物，用于治疗、预防、治疗或改善对中性粒细胞氧化爆发刺激、角质细胞IL-8释放刺激或坏死诱导反应敏感的疾病或病情，可以单独使用或与一个或多个其他药物活性化合物结合使用。