12-氧代-9(2)-十八碳烯-11-内酯 | 114416-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: 12-氧代-9(2)-十八碳烯-11-内酯
• 中文别名: 12-酮-9(2)-十八碳烯-11-交酯
• 英文名称: (9Z)-12-oxooctadec-9-en-11-olide
• 英文别名: (9Z)-12-oxo-9-octadecen-11-olide；(10Z)-12-heptanoyl-1-oxacyclododec-10-en-2-one
• CAS: 114416-54-5
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: TXHNLEIEJZFRRG-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  6
• 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：

  (9Z,11E)-12,13-epoxyoctadeca-9,11-dienoic acid 以 正己烷 为溶剂， 生成 12-氧代-9(2)-十八碳烯-11-内酯
  参考文献：
  名称：

  Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate

  摘要：

  Allene oxide, (9Z, I I F)-12,13-epoxy-9,11-octadecadienoic acid (12,13-EOD), was prepared by incubation of linoleic acid (13S)-hydroperoxide with flaxseed allene oxide synthase (AOS) and purified (as methyl ester) by low temperature HPLC. Identification of pure 12,13-EOD was substantiated by its UV and H-1 NMR spectra and by GC-MS data for its methanol trapping product. The methyl ester of 12,13-EOD (but not the free carboxylic acid) is slowly cyclized in hexane solution, affording a novel cyclopentenone cis- 12-oxo-10-phytoenoic acid. Free carboxylic form of 12,13-EOD does not cyclize due to the exceeding formation of macrolactone (9Z)-12-oxo-9-octadecen-11-olide. The spontaneous cyclization of pure natural allene oxide (12,13-EOD) into cis-cyclopentenone have been observed first time. (c) 2007 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2007.04.010

文献信息

• Geometrical Configuration of 12,13-Epoxyoctadeca-9,11-dienoic Acid, a Product of the Reaction Catalyzed by Flaxseed Allene Oxide Synthase (CYP74A)
  作者：N. V. Medvedeva、Sh. K. Latypov、A. A. Balandina、L. Sh. Mukhtarova、A. N. Grechkin

  DOI：10.1007/s11171-005-0083-8

  日期：2005.11

  short-living allene oxide reaction product that arises under the catalysis by flaxseed allene oxide synthase (CYP74A) was studied by NMR spectroscopy. The structure of (9Z, 11E)-12,13-epoxyoctadeca-9,11-dienoic acid was established for it from the results of the nuclear Overhauser effect measurements.

  通过 NMR 光谱研究了在亚麻籽丙二烯氧化合酶 (CYP74A) 催化下产生的短寿命丙二烯氧化反应产物的几何构型。(9Z, 11E)-12,13-epoxyoctadeca-9,11-dienoic acid 的结构是根据核 Overhauser 效应测量结果确定的。
• Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate
  作者：Natalia V. Medvedeva、Lucia S. Mukhtarova、Faina K. Mukhitova、Alsu A. Balandina、Shamil K. Latypov、Alexander N. Grechkin

  DOI：10.1016/j.chemphyslip.2007.04.010

  日期：2007.8

  Allene oxide, (9Z, I I F)-12,13-epoxy-9,11-octadecadienoic acid (12,13-EOD), was prepared by incubation of linoleic acid (13S)-hydroperoxide with flaxseed allene oxide synthase (AOS) and purified (as methyl ester) by low temperature HPLC. Identification of pure 12,13-EOD was substantiated by its UV and H-1 NMR spectra and by GC-MS data for its methanol trapping product. The methyl ester of 12,13-EOD (but not the free carboxylic acid) is slowly cyclized in hexane solution, affording a novel cyclopentenone cis- 12-oxo-10-phytoenoic acid. Free carboxylic form of 12,13-EOD does not cyclize due to the exceeding formation of macrolactone (9Z)-12-oxo-9-octadecen-11-olide. The spontaneous cyclization of pure natural allene oxide (12,13-EOD) into cis-cyclopentenone have been observed first time. (c) 2007 Elsevier Ireland Ltd. All rights reserved.