11,12-dibromo-drim-5,8(9)-dien-7-one | 176238-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11,12-dibromo-drim-5,8(9)-dien-7-one
• 英文别名: 11,12-dibromodrima-5,8-dien-7-one；11,12-dibromo-5,8(9)-dien-7-one；(4aS)-3,4-bis(bromomethyl)-4a,8,8-trimethyl-5,6,7,8-tetrahydronaphthalen-2(4aH)-one；(4aS)-3,4-bis(bromomethyl)-4a,8,8-trimethyl-6,7-dihydro-5H-naphthalen-2-one
• CAS: 176238-62-3
• 化学式: C₁₅H₂₀Br₂O
• 分子量: 376.131
• InChiKey: RZDOUTIADFFOBS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11,12-dibromo-drim-5,8(9)-dien-7-one 在 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 11,12-dihydroxydrima-5,8-dien-7-one
  参考文献：
  名称：

  摘要：

  The natural drimane sesquiterpenoid lactone 5,6-dehydro-7-oxoisodrimenin was synthesized from drim-8-en-7-one as well as from 7-oxoisodrimenin.

  DOI：

  10.1023/a:1023404126195
• 作为产物：
  描述：

  (R)-methyl 2-(2,5,5,8a-tetramethyl-3-oxo-3,5,6,7,8,8a-hexahydronaphthalen-1-yl)acetate 在 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 乙醇 、 水 、 乙二醇 为溶剂， 反应 5.75h， 生成 11,12-dibromo-drim-5,8(9)-dien-7-one
  参考文献：
  名称：

  Synthesis of drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives from norambreinolide

  摘要：

  A method was elaborated for the synthesis of polyfunctional compounds of the drimane series, viz., drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives, potential intermediates for the synthesis of natural biologically active drimane sesquiterpenoids starting from norambreinolide. The key intermediate of the above drimane compounds is methyl 7-oxo-11-homodrim-8(9)-en-12-oate, prepared by electrochemical oxidation of a mixture of isomeric methyl bicyclohomofamesenoates obtained from norambreinolide.

  DOI：

  10.1007/bf01433763

文献信息

• Synthesis, antibacterial, and antifungal activities of new drimane sesquiterpenoids with azaheterocyclic units
  作者：Aculina Aricu、Alexandru Ciocarlan、Lidia Lungu、Alic Barba、Sergiu Shova、Gheorghita Zbancioc、Ionel I. Mangalagiu、Michele D’Ambrosio、Nicoleta Vornicu

  DOI：10.1007/s00044-016-1665-0

  日期：2016.10

  In order to find new biologically active compounds and in continuation of our work on the synthesis of the novel compounds containing both terpenic and heterocyclic fragments, herein we report the synthesis and assessment of the in vitro antifungal and antibacterial activities of some new drimane sesquiterpenoids with azaheterocyclic fragments. The structures of the synthesized compounds were confirmed

  为了找到新的生物活性化合物，并在我们继续合成包含萜烯和杂环片段的新型化合物的工作中，我们在此报告了一些新的具有氮杂杂环的drimane倍半萜类化合物的体外抗真菌和抗菌活性的合成和评估。碎片。使用核磁共振波谱，质谱，气相色谱和单晶X射线衍射分析确认了合成化合物的结构。进行了微波辅助转换与经典条件的比较研究。已评估了具有氮杂杂环骨架的drimane倍半萜类化合物的体外抗真菌和抗菌活性。分别为-3和3.2×10 -2  µg / ml，在MIC值为1.5 µg / ml时具有另一种良好的抗真菌活性。还报道了与提到的生物活性有关的构效关系。
• ——
  作者：P. F. Vlad

  DOI：10.1023/a:1023404126195

  日期：——

  The natural drimane sesquiterpenoid lactone 5,6-dehydro-7-oxoisodrimenin was synthesized from drim-8-en-7-one as well as from 7-oxoisodrimenin.
• Synthesis of drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives from norambreinolide
  作者：M. N. Koltsa、G. N. Mironov、S. T. Malinovskii、P. F. Vlad

  DOI：10.1007/bf01433763

  日期：1996.1

  A method was elaborated for the synthesis of polyfunctional compounds of the drimane series, viz., drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives, potential intermediates for the synthesis of natural biologically active drimane sesquiterpenoids starting from norambreinolide. The key intermediate of the above drimane compounds is methyl 7-oxo-11-homodrim-8(9)-en-12-oate, prepared by electrochemical oxidation of a mixture of isomeric methyl bicyclohomofamesenoates obtained from norambreinolide.