(RS)-4-methoxy-5-methyl-5H-furan-2-one | 69556-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (RS)-4-methoxy-5-methyl-5H-furan-2-one
• 英文别名: 4-methoxy-5-methyl-5H-furan-2-one；4-Methoxy-5-methylfuran-2(5H)-on；3-methoxy-2-methyl-2H-furan-5-one
• CAS: 69556-71-4
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: RMYKKCMTEOYQRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  12-13 °C
• 沸点：
  110 °C(Press: 0.5 Torr)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-4-methoxy-5-methyl-5H-furan-2-one 在 硫酸 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (1RS,4RS,9RS)-4,9-dimethyl-4-phenylsulfanyl-2,5-dioxa-tricyclo[7.3.1.0^3,7]trideca-3⁽⁷⁾,11-diene-6,8-dione
  参考文献：
  名称：

  Tetrodecamycin 的合成研究：抗生素核心结构的有效方法

  摘要：

  已经开发了一种有效的合成途径，用于聚酮类抗生素四十二霉素 (la) 的核心结构 5。我们的方法的特点是酸催化环化叔丁基二甲基甲硅烷基保护的甲基 α-(γ-羟基酰基) tetronate，导致 5 展示的新型三环骨架。对这个关键闭环步骤的机制的深入了解获得了。此外，已经公开了基于氟离子诱导的脱甲硅烷基化-环化序列的该环骨架的替代途径。

  DOI：

  10.1055/s-2002-32952
• 作为产物：
  描述：

  4-甲氧基-呋喃酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (RS)-4-methoxy-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Toward the synthesis of the antibiotic tetrodecamycin

  摘要：

  We report here a short approach to a tricyclic substructure of tetrodecamycin exhibiting a unique ring skeleton utilising an acid catalysed ring closure as the key step. In addition an efficient three-step synthesis of 5-alkylidene 4-methoxy-2(5H)-furanones starting from 4-methoxy-2(5H)-furanone is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01809-8

文献信息

• Highly Regioselective 3-Hydroxyalkylations of Boron 4-Methoxy-2-furanolates: A New Entry to 5-Unsubstituted and 5-Monosubstituted 3-Acyl-4-O-Methyl Tetronates
  作者：Franz F. Paintner、Lars Allmendinger、Gerd Bauschke

  DOI：10.1055/s-2001-18071

  日期：——

  Boron 4-methoxy-2-furanolates generated in situ from 5-unsubstituted and 5-monosubstituted 4-O-methyl tetronates undergo highly regioselective 3-hydroxyalkylations with aldehydes to give 5-unsubstituted and 5-monosubstituted 3-acyl-4-O-methyl tetronates, respectively, in good overall yields after oxidation of the intermediate alcohols with 2-iodoxybenzoic acid.

  由 5-未取代和 5-单取代的 4-O- 甲基四硼酸酯原位生成的 4-甲氧基-2-呋喃醇酸硼酯与醛发生高区域选择性 3-羟基烷基化反应，生成 5-未取代和 5-单取代的 3-酰基-4-O-甲基四硼酸酯，中间醇与 2-iodoxybenzoic acid 氧化后，总产率良好。
• Gelin, Suzanne; Pollet, Patrick, Synthetic Communications, 1980, vol. 10, # 11, p. 805 - 812
  作者：Gelin, Suzanne、Pollet, Patrick

  DOI：——

  日期：——
• Paintner, Franz F.; Allmendinger, Lars; Bauschke, Gerd, Synlett, 2003, # 1, p. 83 - 86
  作者：Paintner, Franz F.、Allmendinger, Lars、Bauschke, Gerd

  DOI：——

  日期：——
• Synthesis and antimicrobial activity of tetrodecamycin partial structures
  作者：Franz F Paintner、Lars Allmendinger、Gerd Bauschke、Caroline Berns、Peter Heisig

  DOI：10.1016/s0968-0896(03)00221-9

  日期：2003.7

  An efficient synthetic approach to the core structure 5 of the novel polyketide antibiotic tetrodecamycin (1) was developed. This approach features the acid-catalyzed cyclization of a tert-butyldimethylsilyl protected methyl alpha-(gamma-hydroxyacyl) tetronate, leading to the novel tricyclic ring skeleton exhibited by 5, and an efficient strategy for the parallel introduction of the cis-diol and exo-methylene function. In addition to 5, diastereomer 26, analogue 6 and several derivatives (16, 27 29) were prepared and evaluated for their antibacterial activities against Staphylococcus aureus (including MRSA) and, Enterococcus faecalis and for their cytotoxic activities against human leukemia cell lines (HL-60, Jurkat T-cells). While compound 5 did not inhibit the growth of the Gram-positive pathogens (MICs > 128 mug mL(-1)), analogue 6 and 2-naphthoyl derivative 27 showed promising antibacterial activities with MICs of 4-16 mug mL(-1). Remarkably, the antibacterial activity of these compounds was paralleled by cytotoxicity (IC50 10-23 muM). The reactive exo-methylene moiety was shown to be crucial, but not sufficient by its own, for both the antibacterial and the cytotoxic activities. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Miyata, Okiko; Schmidt, Richard R., Angewandte Chemie, 1982, vol. 94, # 8, p. 651 - 652
  作者：Miyata, Okiko、Schmidt, Richard R.

  DOI：——

  日期：——