(5S)-3-(12'-formyldodecyl)-5-methyl-2,5-dihydrofuran-2-one | 156764-90-8

• 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: (5S)-3-(12'-formyldodecyl)-5-methyl-2,5-dihydrofuran-2-one
• 英文别名: (+)-squamostanal-A；squamostanal-A；(5S)-2,5-Dihydro-5-methyl-2-oxo-3-furantridecanal；13-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tridecanal
• CAS: 156764-90-8
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: CWCAGZXBGYHWNE-INIZCTEOSA-N

物化性质

• 沸点：
  441.7±18.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环十五内酯 在 重铬酸吡啶 、 三甲基氯硅烷 、 双氧水 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (5S)-3-(12'-formyldodecyl)-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  （+）-squamostanal-A的合成：番荔枝科的一种生物活性产黄素

  摘要：

  从商业上可得的起始原料以4个步骤合成了Squamostanal-A（5 S -3-（12-甲酰基十二烷基）-5-甲基-2,5-二氢呋喃-2-酮）。这种假天然化合物，可能是番荔枝科产乙酸素的一种氧化产物，可以用作合成solamin或squamocin的有用合成子。

  DOI：

  10.1016/0040-4039(96)00064-0

文献信息

• Synthesis of Squamostanal-A
  作者：Hiroyuki Konno、Hidefumi Makabe、Akira Tanaka、Takayuki Oritani

  DOI：10.1271/bbb.60.526

  日期：1996.1

  The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, which corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'- yloxy]-2-tridecyn-l-ol (5). The NaHMDS-based coupling reaction of 7 with γ-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1

  本文描述了作为四氢呋喃苷元降解产物分离出来的角鲨烷-A（1）的首次合成。碘化物 7 与 1 的潜在醛基相对应，它是由 13-[四氢吡喃-2'-氧基]-2-十三炔-l-醇（5）通过两步法制备的。7 与γ-内酯 8 发生基于 NaHMDS 的偶联反应，得到化合物 9，并通过 3 步顺序将其转化为 1
• Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata
  作者：Hiroyuki Konno、Yasuhiro Okuno、Hidefumi Makabe、Kazuto Nosaka、Akio Onishi、Yoshinari Abe、Atsuya Sugimoto、Kenichi Akaji

  DOI：10.1016/j.tetlet.2007.11.190

  日期：2008.1

  Total synthesis of cis-solamin A was accomplished without using protecting groups starting from (-)-muricatacin in 11 steps with an overall yield of 4.5%. The backbone of cis-solamin A was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-squamostanal-A: a bioactive acetogenin of Annonaceae
  作者：Xavier Franck、Bruno Figadère、André Cavé

  DOI：10.1016/0040-4039(96)00064-0

  日期：1996.3

  5-dihydrofuran-2-one) was synthesized in 4 steps from a commercially available starting material. This pseudo-natural compound, probably an oxidation product of acetogenins of Annonaceae, may serve as a useful synthon for the total synthesis of solamin or squamocin.

  从商业上可得的起始原料以4个步骤合成了Squamostanal-A（5 S -3-（12-甲酰基十二烷基）-5-甲基-2,5-二氢呋喃-2-酮）。这种假天然化合物，可能是番荔枝科产乙酸素的一种氧化产物，可以用作合成solamin或squamocin的有用合成子。