5-methyl-1-(5-methylfuran-2-yl)hex-4-en-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-methyl-1-(5-methylfuran-2-yl)hex-4-en-1-ol
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: XFWGVGZQSQWHEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(5-methylfuran-2-yl)hex-4-en-1-ol 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 magnesium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 74.0h， 生成 1-methyl-3-[(5-methylfuran-2-yl)-2-(4-methylpent-3-enyl)cyclopenta-2,4-dien]-1-ol
  参考文献：
  名称：

  Synthesis of the core framework of the proposed structure of sargafuran

  摘要：

  Synthesis of 2-homoprenyl-1-methyl-3-(5-methylfuran-2-yl)cyclopenta-2,4-dien-1-ol, the core framework of the proposed structure of the brown alga derived natural product sargafuran, was achieved in six steps from the commercially available 5-methylfurfural via the Piancatelli rearrangement of furylcarbinol. The concise synthetic route to the 1,2,3-trisubstituted cyclopentadienol is established. However, the H-1 and C-13 NMR spectral data of the synthetic analog of sargafuran suggest that the originally proposed structure of sargafuran must be incorrect. In addition, the structure of the natural sargafuran is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.052
• 作为产物：
  描述：

  5-甲基呋喃醛 、 5-溴-2-甲基-2-戊烯 在 magnesium 作用下， 以 乙醚 、 1,2-二溴乙烷 为溶剂， 反应 1.5h， 以93%的产率得到5-methyl-1-(5-methylfuran-2-yl)hex-4-en-1-ol
  参考文献：
  名称：

  Synthesis of the core framework of the proposed structure of sargafuran

  摘要：

  Synthesis of 2-homoprenyl-1-methyl-3-(5-methylfuran-2-yl)cyclopenta-2,4-dien-1-ol, the core framework of the proposed structure of the brown alga derived natural product sargafuran, was achieved in six steps from the commercially available 5-methylfurfural via the Piancatelli rearrangement of furylcarbinol. The concise synthetic route to the 1,2,3-trisubstituted cyclopentadienol is established. However, the H-1 and C-13 NMR spectral data of the synthetic analog of sargafuran suggest that the originally proposed structure of sargafuran must be incorrect. In addition, the structure of the natural sargafuran is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.052

文献信息

• Synthesis of the core framework of the proposed structure of sargafuran
  作者：Ryo Katsuta、Kazuya Aoki、Arata Yajima、Tomoo Nukada

  DOI：10.1016/j.tetlet.2012.11.052

  日期：2013.1

  Synthesis of 2-homoprenyl-1-methyl-3-(5-methylfuran-2-yl)cyclopenta-2,4-dien-1-ol, the core framework of the proposed structure of the brown alga derived natural product sargafuran, was achieved in six steps from the commercially available 5-methylfurfural via the Piancatelli rearrangement of furylcarbinol. The concise synthetic route to the 1,2,3-trisubstituted cyclopentadienol is established. However, the H-1 and C-13 NMR spectral data of the synthetic analog of sargafuran suggest that the originally proposed structure of sargafuran must be incorrect. In addition, the structure of the natural sargafuran is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.