methyl 12-bromo-13-nitro-7-oxo-dehydrodeisopropylabietate | 41437-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 12-bromo-13-nitro-7-oxo-dehydrodeisopropylabietate
• 英文别名: methyl 12-bromo-13-nitro-7-oxo-deisopropyldehydroabietate；methyl (1R,4aS,10aR)-6-bromo-1,4a-dimethyl-7-nitro-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylate
• CAS: 41437-48-3
• 化学式: C₁₈H₂₀BrNO₅
• 分子量: 410.264
• InChiKey: JJMRJRJOCVWTMZ-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 12-bromo-13-nitro-7-oxo-dehydrodeisopropylabietate 、 2-萘硼酸 在 palladium diacetate potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到methyl 12-(2-naphthyl)-13-amino-7-oxo-dehydrodeisopropylabietate
  参考文献：
  名称：

  在钯催化的Suzuki交叉偶联反应中同时还原硝基至氨基

  摘要：

  开发了一种有效的钯催化铃木交叉偶联反应，同时还原硝基至氨基的方法。该方法使硝基取代的芳基卤化物易于与芳基硼酸反应，以低至优异的产率提供芳基取代的苯胺。在大气压下，在DMF / H 2 O（5/1）中存在K 2 CO 3（3当量）的情况下，在大气压下，通过Pd（OAc）2（3 mol％）催化反应。

  DOI：

  10.1016/j.tetlet.2008.02.082
• 作为产物：
  描述：

  脱氢松香酸 在 chromium(VI) oxide 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 硝酸 作用下， 以 丙酮 为溶剂， 生成 methyl 12-bromo-13-nitro-7-oxo-dehydrodeisopropylabietate
  参考文献：
  名称：

  Synthesis and metal ion binding activity of methyl 12-amino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives

  摘要：

  Starting from dehydrobaietic acid with the analogous structure of carnosic acid, the intermediate methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate was synthesized through methylation, bromination, carbonylation, and nitration. Subsequently, the coupling of methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate with aliphatic or aromatic primary amine by Ullmann condensation reaction produced a series of methyl 12-imino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives. In order to probe their antioxidant effects through metal ion chelation mechanism, the metal ion binding abilities on Cu2+ and Fe2+ of these compounds were studied using fluorescence quenching method. The results indicated that each compound showed obvious chelation activity with the binding constants (K (A)) of the 10(2) L mol(-1) order of magnitude, which implied its potential pharmacology application as antioxidant by the inhibition of Feton reaction through chelation with Cu2+ and Fe2+.

  DOI：

  10.1007/s00044-011-9766-2

文献信息

• Simultaneous reduction of nitro- to amino-group in the palladium-catalyzed Suzuki cross-coupling reaction
  作者：Heng-Shan Wang、Ying-Chun Wang、Ying-Ming Pan、Shu-Lin Zhao、Zhen-Feng Chen

  DOI：10.1016/j.tetlet.2008.02.082

  日期：2008.4

  An efficient method for palladium-catalyzed Suzuki cross-coupling reaction with simultaneous reduction of nitro- to amino-group has been developed. This method allows nitro-substituted aryl halides to readily react with arylboronic acids, to afford aryl substituted aniline in low to excellent yields. The reaction was catalyzed by Pd(OAc)2 (3 mol %) at 150 °C under atmospheric pressure in the presence

  开发了一种有效的钯催化铃木交叉偶联反应，同时还原硝基至氨基的方法。该方法使硝基取代的芳基卤化物易于与芳基硼酸反应，以低至优异的产率提供芳基取代的苯胺。在大气压下，在DMF / H 2 O（5/1）中存在K 2 CO 3（3当量）的情况下，在大气压下，通过Pd（OAc）2（3 mol％）催化反应。
• Synthesis and metal ion binding activity of methyl 12-amino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives
  作者：Kai Wang、Xianxian Liu、Xianghui Yi、Hengshan Wang、Ye Zhang、Yingming Pan

  DOI：10.1007/s00044-011-9766-2

  日期：2012.9

  Starting from dehydrobaietic acid with the analogous structure of carnosic acid, the intermediate methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate was synthesized through methylation, bromination, carbonylation, and nitration. Subsequently, the coupling of methyl 12-bromo-13-nitro-7-oxo dehydrodeisopropylabietate with aliphatic or aromatic primary amine by Ullmann condensation reaction produced a series of methyl 12-imino-13-nitro-7-oxo dehydrodeisopropylabietate derivatives. In order to probe their antioxidant effects through metal ion chelation mechanism, the metal ion binding abilities on Cu2+ and Fe2+ of these compounds were studied using fluorescence quenching method. The results indicated that each compound showed obvious chelation activity with the binding constants (K (A)) of the 10(2) L mol(-1) order of magnitude, which implied its potential pharmacology application as antioxidant by the inhibition of Feton reaction through chelation with Cu2+ and Fe2+.
• Syntheses, characterization and fluorescent properties of two series of dehydroabietic acid C-ring derivatives
  作者：Yingchun Wang、Chunhua Su、Fangyao Li、Luzhi Liu、Yingming Pan、Xiurong Wu、Hengshan Wang

  DOI：10.1016/j.saa.2010.03.014

  日期：2010.8

  Two series of dehydroabietic acid C-ring derivatives, nitrogen-containing heterocycles (6a-9b) and C-12 substituted compounds (10a-11b), were synthesized and characterized by element analysis, IR, NMR and MS. The UV-vis absorption and fluorescence spectral characteristics of these compounds have been comparatively investigated, and their fluorescence quantum yields were further evaluated. Compared to dehydroabietic acid 1. the absorption and emission spectra of these compounds were bathochromically shifted due to the multiple aromatic rings with rigid planar structures or the larger conjugation of benzene moiety. (C) 2010 Elsevier B.V. All rights reserved.