(6aS,12aS,2'R,3'S)-3',4'-epoxyrotenone | 41993-94-6

• 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: (6aS,12aS,2'R,3'S)-3',4'-epoxyrotenone
• 英文别名: (6aS,12aS,5'R,6'S)-6',7'-Epoxyrotenone；rotenone epoxide；(6'S)-6',7'-epoxyrotenone；(1S,6R,13S)-16,17-dimethoxy-6-[(2S)-2-methyloxiran-2-yl]-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• CAS: 41993-94-6
• 化学式: C₂₃H₂₂O₇
• 分子量: 410.423
• InChiKey: FDCSARIFDWFXCU-UGTOYMOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6aS,12aS,2'R,3'S)-3',4'-epoxyrotenone 在 lithium aluminium deuteride 、 aluminum isopropoxide 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 4.0h， 生成 (6aS,12aS,5'R,6'S)-<7'-2H>Dalpanol
  参考文献：
  名称：

  Crombie, Leslie; Kilbee, Geoffrey W.; Moffatt, Frank, Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3143 - 3148

  摘要：

  DOI：
• 作为产物：
  描述：

  鱼藤酮 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 (6aS,12aS,2'R,3'S)-3',4'-epoxyrotenone 、 (6aS,12aS,2'R,3'R)-3',4'-epoxyrotenone
  参考文献：
  名称：

  Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs

  摘要：

  Bioassay-guided fractionation of the ethyl acetate extract of Ruta graveolens roots yielded rutacridone epoxide with potent selective algicidal activity towards the 2-methyl-isoborneol (MIB)-producing blue-green alga Oscillatoria perornata, with relatively little effect on the green alga Selenastrum capricornutum. The diol-analog of rutacridone epoxide, gravacridondiol, which was also present in the same extract, had significantly less activity towards O. perornata. Rutacridone epoxide also showed significantly higher activity than commercial fungicides captan and benomyl in our micro-bioassay against the agriculturally important pathogenic fungi Colletotrichum fragariae, C. gloeosporioides, C. acutatum, and Botrytis cineara and Fusarium oxysporium. Rutacridone epoxide is reported as a direct-acting mutagen, precluding its use as an agrochemical. In order to understand the structure-activity relationships and to develop new potential biocides without toxicity and mutagenicity, some analogs containing the (2-methyloxiranyl)-dihydrobenzofuran moiety with an epoxide were synthesized and tested. None of the synthetic analogs showed comparable activities to rutacridone epoxide. The absolute stereochemistry of rutacridone was determined to be 2'(R) and that of rutacridone epoxide to be 2'(R), 3'(R) by CD and NMR analysis. Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2005.09.019

文献信息

• Structure and stereochemistry of psorospermin and related cytotoxic dihydrofuranoxanthones from Psorospermum febrifugum
  作者：A. M. Habib、David K. Ho、S. Masuda、T. McCloud、K. S. Reddy、M. Aboushoer、A. McKenzie、S. R. Byrn、Ching Jer Chang、John M. Cassady

  DOI：10.1021/jo00379a018

  日期：1987.2
• Crombie, Leslie; Kilbee, Geoffrey W.; Moffatt, Frank, Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3143 - 3148
  作者：Crombie, Leslie、Kilbee, Geoffrey W.、Moffatt, Frank、Proudfoot, Geoffrey、Whiting, Donald A.

  DOI：——

  日期：——
• Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs
  作者：Kumudini M. Meepagala、Kevin K. Schrader、David E. Wedge、Stephen O. Duke

  DOI：10.1016/j.phytochem.2005.09.019

  日期：2005.11

  Bioassay-guided fractionation of the ethyl acetate extract of Ruta graveolens roots yielded rutacridone epoxide with potent selective algicidal activity towards the 2-methyl-isoborneol (MIB)-producing blue-green alga Oscillatoria perornata, with relatively little effect on the green alga Selenastrum capricornutum. The diol-analog of rutacridone epoxide, gravacridondiol, which was also present in the same extract, had significantly less activity towards O. perornata. Rutacridone epoxide also showed significantly higher activity than commercial fungicides captan and benomyl in our micro-bioassay against the agriculturally important pathogenic fungi Colletotrichum fragariae, C. gloeosporioides, C. acutatum, and Botrytis cineara and Fusarium oxysporium. Rutacridone epoxide is reported as a direct-acting mutagen, precluding its use as an agrochemical. In order to understand the structure-activity relationships and to develop new potential biocides without toxicity and mutagenicity, some analogs containing the (2-methyloxiranyl)-dihydrobenzofuran moiety with an epoxide were synthesized and tested. None of the synthetic analogs showed comparable activities to rutacridone epoxide. The absolute stereochemistry of rutacridone was determined to be 2'(R) and that of rutacridone epoxide to be 2'(R), 3'(R) by CD and NMR analysis. Published by Elsevier Ltd.