methyl (3R,4R)-(+)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl (3R,4R)-(+)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate
• 英文别名: α-methylparaconic acid methyl ester；methylparaconic acid methyl ester；methyl (3R,4R)-4-methyl-5-oxooxolane-3-carboxylate
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: ACDNZGUZZBKZHX-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-5-氧代四氢-3-呋喃羧酸 在 sodium hydroxide 、 三甲基氯硅烷 、 phosphate buffer 、 α-chymotrypsin 作用下， 反应 14.45h， 生成 methyl (3R,4R)-(+)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  A combined experimental and computational strategy in the assignment of absolute configurations of 4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acids and their esters

  摘要：

  Enantiopure cis- and trans-4-methylparaconic acids and their alkyl esters were synthesized by a procedure involving the kinetic enzymatic resolution of diastereomeric lactonic esters. Thus, ethyl cis- and trans-4-methyl-5-oxo-tetrahydrofuran-3-carboxylates were isolated, at high conversion values, with 99% ee from the hydrolyses with HLAP and alpha-CT, respectively. The corresponding enantiopure cis- and trans-lactonic acids were also obtained. The absolute configurations of the products were assigned by chemical correlation, by analysis of their circular dichroism spectra and by electronic structure calculations. All three methodologies lead to the same assignment for the species considered, another example of successful interplay between experiment and theory. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.08.018

文献信息

• Caspase-1 Inhibitors from an Extremophilic Fungus That Target Specific Leukemia Cell Lines
  作者：Andrea A. Stierle、Donald B. Stierle、Teri Girtsman

  DOI：10.1021/np200414c

  日期：2012.3.23

  Berkeley Pit Lake, Butte, Montana, is a 540 m deep abandoned open-pit copper mine filled with over 140 billion liters of acidic, metal-sulfate-contaminated water. This harsh environment has yielded several microorganisms that produce interesting biologically active compounds. Several polyketide metabolites including the new berkazaphilones A (1) and B (2) and octadienoic acid derivatives berkedienoic acid (13) and berkedienolactone (15), as well as previously reported azaphilone 4, vermistatin (6), dihydrovermistatin (7), penisimplicissin (8), aldehyde 9, and methylparaconic acid (11), were isolated from a culture broth of Penicillium rubrum taken from a depth of 270 m. The structures of these compounds were deduced by interpretation of spectroscopic data. The compounds were isolated either for their inhibition of the signal transduction enzyme caspase-1 or because of their structural similarity to these inhibitors. Selected compounds were further evaluated for their ability to inhibit interleukin-1 beta production by inflammasomes in induced THP-1 cells. Berkazaphilones B (2) and C (4) and vermistatin analogue penisimplicissin (8) exhibited selective activity against leukemia cancer cell lines in tha National Cancer Institute 60 human cell line assay.
• A combined experimental and computational strategy in the assignment of absolute configurations of 4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acids and their esters
  作者：Cristina Forzato、Giada Furlan、Patrizia Nitti、Giuliana Pitacco、Domenico Marchesan、Sonia Coriani、Ennio Valentin

  DOI：10.1016/j.tetasy.2005.08.018

  日期：2005.9

  Enantiopure cis- and trans-4-methylparaconic acids and their alkyl esters were synthesized by a procedure involving the kinetic enzymatic resolution of diastereomeric lactonic esters. Thus, ethyl cis- and trans-4-methyl-5-oxo-tetrahydrofuran-3-carboxylates were isolated, at high conversion values, with 99% ee from the hydrolyses with HLAP and alpha-CT, respectively. The corresponding enantiopure cis- and trans-lactonic acids were also obtained. The absolute configurations of the products were assigned by chemical correlation, by analysis of their circular dichroism spectra and by electronic structure calculations. All three methodologies lead to the same assignment for the species considered, another example of successful interplay between experiment and theory. (C) 2005 Published by Elsevier Ltd.