(5R)-3-[(1S)-1-hydroxyethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-4-methylfuran-2(5H)-one | 565434-37-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R)-3-[(1S)-1-hydroxyethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-4-methylfuran-2(5H)-one
• CAS: 565434-37-9
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: UMEIHRPYUQPCHU-WAUSDMSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5R)-3-[(1S)-1-hydroxyethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-4-methylfuran-2(5H)-one 在 sodium tetrahydroborate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-[(1S)-1-hydroxyethyl]-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
• 作为产物：
  描述：

  (5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮 、 乙醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以23%的产率得到(5R)-3-[(1S)-1-hydroxyethyl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-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

• 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.