(8'EZ)-3-(iodonon-9'-enyl)-5-methyl-2,5-dihydrofuran-2-one | 676352-00-4

• 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: (8'EZ)-3-(iodonon-9'-enyl)-5-methyl-2,5-dihydrofuran-2-one
• 英文别名: (5S)-3-(9-Iodonon-8-en-1-yl)-5-methylfuran-2(5H)-one；(2S)-4-(9-iodonon-8-enyl)-2-methyl-2H-furan-5-one
• CAS: 676352-00-4
• 化学式: C₁₄H₂₁IO₂
• 分子量: 348.224
• InChiKey: RXCMXTPUWLQNBP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8'EZ)-3-(iodonon-9'-enyl)-5-methyl-2,5-dihydrofuran-2-one 、 (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-yn-1-ol 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 5.0h， 生成 (S)-3-{(E)-(R)-13-Hydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridec-8-en-10-ynyl}-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Essential structural features of acetogenins: role of hydroxy groups adjacent to the bis-THF rings

  摘要：

  The presence of two hydroxy groups adjacent to the THF ring(s) is a common structural feature of natural acetogenins. To elucidate the role of each hydroxy group in the inhibitory action of acetogenins, we synthesized three acetogenin analogues which lack either or both of the hydroxy groups, and investigated their inhibitory activities with bovine heart mitochondrial complex I. Our results indicate that the presence of either of the two hydroxy groups sufficiently sustains a potent inhibitory effect. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.021
• 作为产物：
  描述：

  (E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one 在 间氯过氧苯甲酸 、 碳酸氢钠 、 sodium thiosulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.33h， 以82%的产率得到(8'EZ)-3-(iodonon-9'-enyl)-5-methyl-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  A Concise Synthesis of Solamin and cis-Solamin, Mono-THF Acetogenins from Annona muricata

  摘要：

  A concise total synthesis of solamin (1) and cis-solamin (2) was performed using an epoxy alcohol (11) as a versatile chiral building block for synthesizing the stereoisomers of the mono-THF annonaceous acetogenins.

  DOI：

  10.3987/com-09-11741

文献信息

• Synthesis of non-THF analogs of acetogenin toward simplified mimics
  作者：Daisuke Fujita、Naoya Ichimaru、Masato Abe、Masatoshi Murai、Takeshi Hamada、Takaaki Nishioka、Hideto Miyoshi

  DOI：10.1016/j.tetlet.2005.05.150

  日期：2005.8

  Acetogenin analogs in which the bis-adjacent THF ring was replaced with an enantioselectively synthesized 1,2-cyclo-pentanediol bis-ether skeleton were synthesized to obtain simplified mimics, and their inhibitory effect on mitochondrial NADH-ubiquinone oxidoreductase (complex I) was examined. The results clearly demonstrate that the 1,2-cyclopentanediol bis-ether motif can substitute for the bis-THF ring while maintaining very potent inhibitory activity at the nanomolar level. (c) 2005 Elsevier Ltd. All rights reserved.
• Syntheses of a Pyrrolidine Analog of a Tetrahydrofuran Containing Acetogenin, cis-Solamin
  作者：Yasunao Hattori、Kouji Ohnishi、Haruka Sakurai、Kazuya Kobayashi、Hidefumi Makabe、Kenta Teruya、Kenichi Akaji

  DOI：10.3987/com-14-13163

  日期：——

  Practical synthesis of a pyrrolidine analog of a mono-THE acetogenin as a proto-type analog to evaluate the effect of a heteroatom in the mono-THF ring of acetogenins was achieved using Pd(II)-catalyzed diastereo-selective cyclization. Ligand-less PdCl2 catalyzed cyclization yielded the desired pyrrolidine derivative as a single major product having the desired relative configurations. Coupling of the pyrrolidine fragment with a known gamma-lactone-containing fragment via a Sonogashira cross-coupling reaction yielded the desired aza-cis-solamin analog.