3-[(1R,2S)-1-hydroxy-2-methylbutyl]-4-methylfuran-2(5H)-one

• 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: 3-[(1R,2S)-1-hydroxy-2-methylbutyl]-4-methylfuran-2(5H)-one
• 英文别名: 4-[(1R,2S)-1-hydroxy-2-methylbutyl]-3-methyl-2H-furan-5-one
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ZXYIUEGERMMVDN-IMTBSYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-甲基丁醛 在 sodium tetrahydroborate 、 三溴化硼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 3-[(1R,2S)-1-hydroxy-2-methylbutyl]-4-methylfuran-2(5H)-one
  参考文献：
  名称：

  Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs

  摘要：

  The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus TU 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00483-6

文献信息

• A Diels-Alder/Retro-Diels-Alder Approach for the Enantioselective Synthesis of Microbial Butenolides
  作者：Christian A. Citron、Susanne M. Wickel、Barbara Schulz、Siegfried Draeger、Jeroen S. Dickschat

  DOI：10.1002/ejoc.201200991

  日期：2012.10.9

  structures were verified by synthesis of reference compounds through a Diels–Alder/retro-Diels–Alder approach. This synthetic method was also successfully applied in the synthesis of butenolides that are signalling molecules from streptomycetes. For the enantioselective synthesis of these butenolides a modified route including an enantioselective Diels–Alder reaction was used.

  已从内生真菌 Geniculosporium sp. 中鉴定出几种挥发性内酯。从岩蔷薇 Cistus monspeliensis 中分离出来，俗称蒙彼利埃岩蔷薇。通过使用闭环汽提装置从琼脂平板培养物中收集真菌挥发物，并通过 GC-MS 分析顶空提取物。这些内酯的结构是从它们的质谱数据中提出的。通过 Diels-Alder/retro-Diels-Alder 方法合成参考化合物来验证建议的结构。这种合成方法也成功地应用于合成链霉菌信号分子丁烯内酯。对于这些丁烯内酯的对映选择性合成，使用了一种改进的路线，包括对映选择性 Diels-Alder 反应。
• Bioactive butenolides from Streptomyces antibioticus TÜ 99: absolute configurations and synthesis of analogs
  作者：Gilles Grossmann、Marc Poncioni、Marc Bornand、Benoı̂t Jolivet、Markus Neuburger、Urs Séquin

  DOI：10.1016/s0040-4020(03)00483-6

  日期：2003.4

  The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus TU 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum. (C) 2003 Elsevier Science Ltd. All rights reserved.