dihydro-3-hydroxy4-methylfuran-2(3H)-one | 4386-18-9

• 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: dihydro-3-hydroxy4-methylfuran-2(3H)-one
• 英文别名: 3-Hydroxy-4-methyloxolan-2-one
• CAS: 4386-18-9
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: GFPAFTLIWBGZMF-UHFFFAOYSA-N

物化性质

• 沸点：
  100-130 °C(Press: 0.03 Torr)
• 密度：
  1.2229 g/cm3(Temp: 4 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydro-3-hydroxy4-methylfuran-2(3H)-one 在 2-碘酰苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 4.5h， 生成 二氢-4-甲基呋喃-2,3-二酮
  参考文献：
  名称：

  Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed

  摘要：

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.

  DOI：

  10.1021/ol8018852
• 作为产物：
  描述：

  二氢-4-甲基 2(3H)-呋喃酮 在 lithium hexamethyldisilazane 、 韦德伊斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以64%的产率得到dihydro-3-hydroxy4-methylfuran-2(3H)-one
  参考文献：
  名称：

  Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed

  摘要：

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.

  DOI：

  10.1021/ol8018852

文献信息

• Biocatalytic Synthesis of Homochiral 2-Hydroxy-4-butyrolactone Derivatives by Tandem Aldol Addition and Carbonyl Reduction
  作者：Carlos J. Moreno、Karel Hernández、Samantha Gittings、Michael Bolte、Jesús Joglar、Jordi Bujons、Teodor Parella、Pere Clapés

  DOI：10.1021/acscatal.3c00367

  日期：2023.4.21

  hydroxymethyltransferase (KPHMTEcoli), 2-keto-3-deoxy-l-rhamnonate aldolase (YfaUEcoli), and trans-o-hydroxybenzylidene pyruvate hydratase-aldolase from Pseudomonas putida (HBPAPputida) and (ii) subsequent 2-oxogroup reduction of the aldol adduct by ketopantoate reductase from E. coli (KPREcoli) and a Δ1-piperidine-2-carboxylate/Δ1-pyrroline-2-carboxylate reductase from Pseudomonas syringae pv. tomato DSM 50315

  手性 2-羟基酸和 2-羟基-4-丁内酯衍生物是精细化学品和商品化学品中常见的结构基序。在这里，我们报告了使用三种立体选择性醛缩酶和两种立体互补酮还原酶使用简单和非手性起始材料制备这些化合物的串联生物催化立体发散途径。该策略包括 (i) 使用来自大肠杆菌的两种醛缩酶、3-甲基-2-氧代丁酸羟甲基转移酶 (KPHMT Ecoli )、2-keto-3-deoxy- l- rhamnonate 醛缩酶 (YfaU) 将 2-含氧酸与醛进行醛醇加成反应大肠杆菌）和来自恶臭假单胞菌的反式-o-羟基亚苄基丙酮酸水合酶-醛缩酶(HBPA Pputida ) 和 (ii) 随后通过来自大肠杆菌(KPR Ecoli )的酮泛解酸还原酶和来自假单胞菌的 Δ 1 -piperidine-2-carboxylate/Δ 1 -pyrroline-2-carboxylate 还原酶对羟醛加合物的 2-氧代还原丁香树_
• Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed
  作者：Vasudha Sharma、Gilbert T. Kelly、Coran M. H. Watanabe

  DOI：10.1021/ol8018852

  日期：2008.11.6

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.