二氢吴茱萸新碱 | 15266-35-0

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 二氢吴茱萸新碱
• 中文别名: 二氢吴茱萸卡品碱
• 英文名称: dihydroevocarpine
• 英文别名: 1-methyl-2-tridecyl-4(1H)-quinolone；1-methyl-2-tridecylquinolin-4-one
• CAS: 15266-35-0
• 化学式: C₂₃H₃₅NO
• 分子量: 341.537
• InChiKey: DWHCRAGHDDLXEM-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69℃
• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8℃，干燥保存，并需密闭。

制备方法与用途

化学性质： 这是一种白色结晶粉末，能溶解于甲醇、乙醇和DMSO等有机溶剂中，来源于吴茱萸（学名：Evodia rutaecarpa （Juss.）Benth.）。

反应信息

• 作为产物：
  描述：

  5-溴戊酸 在 10% palladium on activated carbon 、 氢气 、 sodium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正庚烷 、 乙基苯 、 甲苯 为溶剂， 反应 81.5h， 生成 二氢吴茱萸新碱
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060

文献信息

• Alkylation of Pyridone Derivatives By Nickel/Lewis Acid Catalysis
  作者：Ryuichi Tamura、Yuuya Yamada、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1002/anie.201200922

  日期：2012.6.4

  MAD as an additive: The [Ni(cod)2], (2,6‐tBu2‐4‐MeC6H2O)2AlMe (MAD), and N‐heterocyclic carbene (NHC) catalytic system effected a highly regioselective alkylation of pyridone derivatives (see scheme). Substituted pyridones and related heterocycles react with both terminal and internal alkenes to selectively give a range of nitrogen‐containing heterocycles with linear alkyl substituents.

  MAD作为添加剂：[Ni（cod）2 ]，（2,6 - t Bu 2-4 -MeC 6 H 2 O）2 AlMe（MAD​​）和N-杂环卡宾（NHC）催化体系产生了很高的吡啶酮衍生物的区域选择性烷基化（参见方案）。取代的吡啶酮和相关的杂环与末端和内部烯烃反应，从而选择性地生成一系列具有线性烷基取代基的含氮杂环。
• Quinolone alkaloids from Evodia rutaecarpa
  作者：Yuan-Qing Tang、Xiao-Zhang Feng、Liang Huang

  DOI：10.1016/0031-9422(96)00304-4

  日期：1996.10

  Five new quinolone alkaloids were isolated from the fruits of Evodia rutaecarpa, together with seven known ones. Their structures were determined on the basis of spectral data and chemical reactions.

  从吴茱萸果实中分离出五种新型喹诺酮类生物碱，以及七种已知的喹诺酮类生物碱。它们的结构是根据光谱数据和化学反应确定的。
• Coppola, Gary M., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 491 - 494
  作者：Coppola, Gary M.

  DOI：——

  日期：——
• SUGIMOTO, TOHRU;MIYASE, TOSHIO;KUROYANAGI, MASANORI;UENO, AKIRA, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4453-4461
  作者：SUGIMOTO, TOHRU、MIYASE, TOSHIO、KUROYANAGI, MASANORI、UENO, AKIRA

  DOI：——

  日期：——
• Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones
  作者：Abraham A. Wube、Antje Hüfner、Christina Thomaschitz、Martina Blunder、Manfred Kollroser、Rudolf Bauer、Franz Bucar

  DOI：10.1016/j.bmc.2010.10.060

  日期：2011.1

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.