6-oxo-6a,12a-dehydrodeguelin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-oxo-6a,12a-dehydrodeguelin
• 英文别名: 17,18-Dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaene-13,22-dione；17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaene-13,22-dione
• 化学式: C₂₃H₁₈O₇
• 分子量: 406.392
• InChiKey: NWWVDLRRSGQBKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 3-(3,4-dimethoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-2-carboxylate 在 dipotassium peroxodisulfate 、 copper(l) iodide 、 lithium hydroxide monohydrate 、 silver nitrate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 19.0h， 生成 6-oxo-6a,12a-dehydrodeguelin
  参考文献：
  名称：

  一种简单的直接去氧氧化羰基脱氢类胡萝卜素的方法，其合成方法包括甾烷酮，​​鱼藤酮，6-羰基脱氢椭圆烯和6-羰基-6a，12a-脱氢deguelin

  摘要：

  据报道，有一种通过异黄酮2-羧酸直接内酯化来构建羰基-脱氢类胡萝卜素的方法。演示了该方法在天然产物首次合成中的应用，该合成物为马酮酮，6-氧代-脱氢Elliptone，鱼藤酮和6-氧代-6a，12a-脱氢deguelin。还评估了一系列氧-脱氢类胡萝卜素的生物活性。

  DOI：

  10.1002/ejoc.201900078

文献信息

• DEGUELIN. I. THE PREPARATION, PURIFICATION AND PROPERTIES OF DEGUELIN, A CONSTITUENT OF CERTAIN TROPICAL FISH-POISONING PLANTS
  作者：E. P. Clark

  DOI：10.1021/ja01352a045

  日期：1931.1.1
• Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei
  作者：François Ngandeu、Merhatibeb Bezabih、Dieudonne Ngamga、Alembert T. Tchinda、Bonaventure T. Ngadjui、Berhanu M. Abegaz、Hanh Dufat、François Tillequin

  DOI：10.1016/j.phytochem.2007.05.038

  日期：2008.1

  Three prenylated rotenoids, elliptol, 12-deoxo-12 alpha-methoxyelliptone and 6-methoxy-6a, 12a-dehydrodeguelin were isolated from the twigs of Millettia duchesnei, together with the known compounds, 6a,12a-dehydrodeguelin, 6-hydroxy-6a, 12a-dehydrodeguelin, 6-oxo-6a, 12a-dehydrodeguelin, elliptone, 12a-hydroxyelliptone and eriodictyol. Their structures were elucidated on the basis of spectral data and comparison with information reported in the literature and with authentic specimens for some known compounds. The full NMR data of 6-oxo-6a, 12a-dehydrodeguelin and 6-hydroxy-6a, 12a-dehydrodeguelin are reported here for the first time. (C) 2007 Elsevier Ltd. All rights reserved.
• A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin
  作者：Jutatip Boonsombat、Sanit Thongnest、Somsak Ruchirawat

  DOI：10.1002/ejoc.201900078

  日期：2019.5.26

  An approach to construct the oxo‐dehydrorotenoids via direct lactonization of isoflavone‐2‐carboxylic acids is reported. The application of this method for the first total syntheses of the natural products, stemonone, 6‐oxo‐dehydroelliptone, rotenonone, and 6‐oxo‐6a,12a‐dehydrodeguelin, are demonstrated. The series of oxo‐dehydrorotenoids was also evaluated for their biological activities.

  据报道，有一种通过异黄酮2-羧酸直接内酯化来构建羰基-脱氢类胡萝卜素的方法。演示了该方法在天然产物首次合成中的应用，该合成物为马酮酮，6-氧代-脱氢Elliptone，鱼藤酮和6-氧代-6a，12a-脱氢deguelin。还评估了一系列氧-脱氢类胡萝卜素的生物活性。