(2S,3R)-3-butyloxirane-2-carboxylic acid | 132665-45-3

• 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: (2S,3R)-3-butyloxirane-2-carboxylic acid
• 英文别名: (2S,3R)-2,3-epoxyheptanoic acid；(2S-trans)-3-butyl-oxiranecarboxylic acid
• CAS: 132665-45-3
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: HOZQSRMTDXZVPJ-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-butyloxirane-2-carboxylic acid 在 aluminum oxide 、 lithium perchlorate 、 1-羟基苯并三唑 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (2R,3S)-2-hydroxy-3-(phenylsulfanyl)heptanoic acid (tetrahydropyran-2-yloxy)amide
  参考文献：
  名称：

  Hydroxamic Acid Derivatives as Potent Peptide Deformylase Inhibitors and Antibacterial Agents

  摘要：

  Low-molecular-weight beta-sulfonyl- and beta-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.

  DOI：

  10.1021/jm000018k
• 作为产物：
  描述：

  (2R,3R)-(3-butyloxiranyl)methyl alcohol 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (2S,3R)-3-butyloxirane-2-carboxylic acid
  参考文献：
  名称：

  Hydroxamic Acid Derivatives as Potent Peptide Deformylase Inhibitors and Antibacterial Agents

  摘要：

  Low-molecular-weight beta-sulfonyl- and beta-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.

  DOI：

  10.1021/jm000018k

文献信息

• Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing alpha-keto amide compound using them
  申请人：Kobayashi Nobuo

  公开号：US20080058516A1

  公开（公告）日：2008-03-06

  The present invention is to provide manufacturing intermediates which can be led to useful α-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide epoxycarboxamide compounds, azide compounds and amino alcohol compounds represented by the following formulae: wherein R 1 and R 2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 3 represents alkyl group, alkenyl group, aromatic hydrocarbon group, heterocyclic group, R 6 —O— or R 7 —N(R 8 )—; where R 6 represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 7 and R 8 each represents hydrogen atom, alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group, and, R 4 and R 5 represent the same groups as R 7 and R 8 , respectively, and R 4 and R 5 optionally form a ring together; and X represents —O— or —N(R 9 )—, where R 9 represents hydrogen atom or alkyl group, and X optionally forms a ring together with R 4 or R 5 , and processes for preparing α-keto amide compound using the same.

  本发明提供了制造中间体，该中间体可以经济、立体选择性地导致有蛋白酶抑制活性的有用α-酮酰胺化合物，并提供了由以下式子表示的环氧羧酰胺化合物、叠氮化合物和氨基醇化合物： 其中，R1和R2分别表示烷基、烯基、芳香族烃基或杂环基；R3表示烷基、烯基、芳香族烃基、杂环基、R6-O-或R7-N(R8)-；其中，R6表示烷基、烯基、芳香族烃基或杂环基；R7和R8分别表示氢原子、烷基、烯基、芳香族烃基或杂环基，而R4和R5分别表示与R7和R8相同的基团，R4和R5可选择性地共同形成环；X表示-O-或-N(R9)-，其中R9表示氢原子或烷基，而X可选择性地与R4或R5共同形成环；以及使用其制备α-酮酰胺化合物的方法。
• Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing α-keto amide compound using them
  申请人：Seikagaku Kogyo Kabushiki Kaisha

  公开号：US08163943B2

  公开（公告）日：2012-04-24

  The present invention is to provide manufacturing intermediates which can be led to useful α-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide epoxycarboxamide compounds, azide compounds and amino alcohol compounds represented by the following formulae: wherein R1 and R2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R3 represents alkyl group, alkenyl group, aromatic hydrocarbon group, heterocyclic group, R6—O— or R7—N(R8)—; where R6 represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R7 and R8 each represents hydrogen atom, alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group, and, R4 and R5 represent the same groups as R7 and R8, respectively, and R4 and R5 optionally form a ring together; and X represents —O— or —N(R9)—, where R9 represents hydrogen atom or alkyl group, and X optionally forms a ring together with R4 or R5, and processes for preparing α-keto amide compound using the same.

  本发明旨在提供制造中间体，可以极具经济性和立体选择性地制备具有蛋白酶抑制活性的有用α-酮酰胺化合物，并提供由以下式表示的环氧羧酰胺化合物、叠氮化合物和氨基醇化合物：其中R1和R2分别表示烷基、烯基、芳香烃基或杂环基；R3表示烷基、烯基、芳香烃基、杂环基、R6—O—或R7—N（R8）—；其中R6表示烷基、烯基、芳香烃基或杂环基；R7和R8分别表示氢原子、烷基、烯基、芳香烃基或杂环基，而R4和R5分别表示与R7和R8相同的基团，R4和R5可以选择性地共同形成环；X表示—O—或—N（R9）—，其中R9表示氢原子或烷基，并且X可以选择性地与R4或R5共同形成环；以及使用它们制备α-酮酰胺化合物的过程。
• EPOXYCARBOXAMIDE COMPOUND, AZIDE COMPOUND, AND AMINO ALCOHOL COMPOUND, AND PROCESS FOR PREPARING a-KETO AMIDE COMPOUND USING THEM
  申请人：KOBAYASHI Nobuo

  公开号：US20120197015A1

  公开（公告）日：2012-08-02

  The present invention is directed to providing epoxycarboxamide compounds, azide compounds and amino alcohol compounds which serve as manufacturing intermediates that can lead to useful α-ketoamide compounds, and the present invention is also is directed to processes for preparing α-ketoamide compounds using the intermediates. The epoxycarboxamide compounds, azide compounds and amino alcohol compounds are represented by the following formulae: wherein R 1 , R 2 , R 3 , R 4 and R 5 , as well as subvariables for one or more of R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein.

  本发明旨在提供作为制造中间体的环氧羧酰胺化合物、叠氮化合物和氨基醇化合物，这些中间体可以导致有用的α-酮酰胺化合物，并且本发明还旨在提供使用这些中间体制备α-酮酰胺化合物的过程。环氧羧酰胺化合物、叠氮化合物和氨基醇化合物由以下式表示：其中R1、R2、R3、R4和R5以及R1、R2、R3、R4和R5中一个或多个的子变量如本文所定义。
• Epoxycarboxylic acid amides, azides and amino alcohols and processes for preparation of alpha-keto amides by using them
  申请人：SEIKAGAKU CORPORATION

  公开号：EP2289887A2

  公开（公告）日：2011-03-02

  The present invention is to provide manufacturing intermediates which can be led to useful α-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide azide compounds represented by the following formula: wherein R1 and R2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; and processes for preparing α-keto amide compound using the same.

  本发明旨在提供可极其经济地、立体选择性地制备出具有蛋白酶抑制活性的有用 α-酮酰胺化合物的中间体，并提供下式所代表的叠氮化合物： 其中 R1 和 R2 分别代表烷基、烯基、芳香烃基或杂环基；以及使用上述化合物制备 α-酮酰胺化合物的工艺。
• Optically active epoxy compounds and processes for their production
  申请人：TOSOH CORPORATION

  公开号：EP1403260B1

  公开（公告）日：2007-08-08