(2R,3R)-potassium 2,3-epoxybutyrate | 84823-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-potassium 2,3-epoxybutyrate
• 英文别名: potassium (2R,3R)-β-methylglycidate；potassium;(2R,3R)-3-methyloxirane-2-carboxylate
• CAS: 84823-47-2
• 化学式: C₄H₅O₃*K
• 分子量: 140.18
• InChiKey: XPJVTPNSXPMUSV-SWLXLVAMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.47
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-氨基-2-萘酚 、 (2R,3R)-potassium 2,3-epoxybutyrate 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以45%的产率得到(2R,3R)-3-Methyl-oxirane-2-carboxylic acid (2-hydroxy-naphthalen-1-yl)-amide
  参考文献：
  名称：

  通过环氧乙烷羧酸和酯与芳香族邻羟基芳基胺的区域控制环转化合成旋光的1,4-苯并恶嗪酮和1,5-苯并恶嗪酮

  摘要：

  对映体二乙基环氧乙烷乙烷二羧酸酯1与邻氨基苯酚2反应生成1,4-苯并恶嗪-2-酮5或与1,5-苯并恶唑啉-2-酮4反应，而缩合的1,4-恶嗪-3-酮6反应。用2-氨基-3-羟基吡啶制得。另一方面，光学活性环氧乙烷羧酸7在DCC（二环己基碳二亚胺）或氯甲酸异丁酯的存在下与邻氨基苯酚8反应，得到环氧乙烷羧酰胺9，其可以被环转化为2,3-二氢-4 H -1,4。 -苯并恶嗪-3-酮10或3-羟基-2,3-二氢-5H -1,5-苯并恶唑啉-4-酮11取决于反应条件。

  DOI：

  10.1016/s0040-4020(99)00488-3
• 作为产物：
  描述：

  (2S,3R)-2-Bromo-3-hydroxybutanoic acid 在 氢氧化钾 作用下， 以 水 为溶剂， 以30 g的产率得到(2R,3R)-potassium 2,3-epoxybutyrate
  参考文献：
  名称：

  Optical rotatory dispersion studies. 135. Synthesis and chiroptical properties of (S)- and (R)-(3-2H1)-2,2-dimethylcyclobutanone. Evidence for conformational effects in substituted cyclobutanones

  摘要：

  DOI：

  10.1021/ja00346a050

文献信息

• Ring Transformation of Glycidic Amides with <i>Ortho</i>-Metalated Phenols to Enantiopure 3-Hydroxychromanones
  作者：Karsten Woydowski、Burkhard Ziemer、Jürgen Liebscher

  DOI：10.1021/jo982242b

  日期：1999.5.1

  A novel access to hitherto unknown enantiopure 2-alkylchroman-4-ones 10 was found by a reaction of ortho-metalated O-MOM-protected phenols with Weinreb amides 8 of enantiopure cis- or trans-glycidic acids, Upon acidic hydrolysis, the resulting o-MOMO-benzoyloxiranes 9 undergo ring transformation to 2-alkylchroman-4-ones 10. 2-Alkylidenecoumaran-3-ones 11 were formed as alternative products, depending on the configuration of the starting oxirane ring and on the type of phenol used as starting material.
• Shiozaki, Masao; Ishida, Noboru; Maruyama, Hiroshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 9, p. 2352 - 2356
  作者：Shiozaki, Masao、Ishida, Noboru、Maruyama, Hiroshi

  DOI：——

  日期：——
• Screening of electrophilic compounds yields an aziridinyl peptide as new active-site directed SARS-CoV main protease inhibitor
  作者：Erika Martina、Nikolaus Stiefl、Björn Degel、Franziska Schulz、Alexander Breuning、Markus Schiller、Radim Vicik、Knut Baumann、John Ziebuhr、Tanja Schirmeister

  DOI：10.1016/j.bmcl.2005.09.012

  日期：2005.12

  The coronavirus main protease, M-pro, is considered a major target for drugs suitable to combat coronavirus infections including the severe acute respiratory syndrome (SARS). In this study, comprehensive HPLC- and FRET-substrate-based screenings of various electrophilic compounds were performed to identify potential M-pro inhibitors. The data revealec that the coronaviral main protease is inhibited by aziridine- and oxirane-2-carboxylates. Among the trans-configured aziridine-2.3-dicarboxylates the Gly-Gly-containing peptide 2c was found to be the most potent inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.
• OIDA, SADAO;TAKEHDA, TADAKO
  作者：OIDA, SADAO、TAKEHDA, TADAKO

  DOI：——

  日期：——
• SHIOZAKI MASAO; ISHIDA NOBORU; MARUYAMA HIROSHI, AGR. AND BIOL. CHEM., 50,(1986) N 9, 2353-2356
  作者：SHIOZAKI MASAO、 ISHIDA NOBORU、 MARUYAMA HIROSHI

  DOI：——

  日期：——