2-(3,6,7-trimethoxyphenanthren-9-ylmethyl)pyrrolidine | 51693-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-(3,6,7-trimethoxyphenanthren-9-ylmethyl)pyrrolidine
• 英文别名: 2-((2,3,6-trimethoxyphenanthren-10-yl)methyl)pyrrolidine；2-<3,6,7-Trimethoxy-phenanthryl-(9)-methyl>-pyrrolidin；2-[(2,3,6-trimethoxy-10-phenanthryl)methyl]pyrrolidine；2-[(3,6,7-Trimethoxyphenanthren-9-yl)methyl]pyrrolidine
• CAS: 51693-23-3
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: AIAJYHJEIXNZGS-UHFFFAOYSA-N

物化性质

• 沸点：
  526.3±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-(3,6,7-trimethoxyphenanthren-9-ylmethyl)pyrrolidine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以97%的产率得到rac-antofine
  参考文献：
  名称：

  氯化铁基菲的轻度合成及其在菲咯啉吲哚并烷生物碱的全合成中的应用

  摘要：

  氯化铁（III）已用于在室温下通过分子内氧化偶合以优异的收率制备聚甲氧基取代的菲-9羧酸。温和的反应条件和使用环保的FeCl 3为重要的菲环的合成提供了一条新颖的实用途径。从易于获得的吡咯开始，分别以48％，44％和46％的总收率实现了该方案作为酪氨酸，脱氧酪氨酸和antofine全面合成关键步骤的进一步应用。这种新的高效策略具有许多优势。该实验过程在温和条件下简单，原子经济性很高，没有任何保护基，原料便宜或易于制备。因此，这种简短实用的方法适用于大规模生产。

  DOI：

  10.1016/j.tet.2008.06.003
• 作为产物：
  描述：

  2,3,6-三甲氧基菲-10-甲醛 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 2-(3,6,7-trimethoxyphenanthren-9-ylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and structure–activity studies of antofine analogues as potential anticancer agents

  摘要：

  Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.080

文献信息

• Synthesis of Phenanthro[9,10-<i>b</i>]indolizidin-9-ones, Phenanthro[9,10-<i>b</i>]quinolizidin-9-one, and Related Benzolactams by Pd(OAc)₂-Catalyzed Direct Aromatic Carbonylation
  作者：Satoshi Yamashita、Nobuhito Kurono、Hisanori Senboku、Masao Tokuda、Kazuhiko Orito

  DOI：10.1002/ejoc.200801047

  日期：2009.3

  10-b]indolizidin-9-ones, phenanthro[9,10-b]quinolizidin-9-one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc)2-catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and -quinolizidine alkaloids (±)-tylophorine, (±)-antofine, and (±)-cryptopleurine.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany

  菲 [9,10-b] indolizidin-9-ones、菲 [9,10-b] quinolizidin-9-one 和相关苯并内酰胺是通过使用 Pd(OAc)2 催化的直接芳香羰基化通过苯内酰胺环形成合成的。这也构成了代表性的菲吲哚里西啶和-喹唑西啶生物碱 (±)-tylophorine、(±)-antofine 和 (±)-cryptopleurine 的正式合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Total syntheses of (±)-cryptopleurine, (±)-antofine and (±)-deoxypergularinine
  作者：Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1016/s0040-4020(99)00017-4

  日期：1999.2

  The alkaloids (±)-cryptopleurine 1, (±)-antofine 2, and (±)-deoxypergularinine 3 were synthesized by Pictet-Spengler cyclization of the 2-arylmethylpiperidine and -pyrrolidines 4, 5 and 6 obtained by sequential N-deprotection-reduction of the parent enecarbamates 7, 8 and 9. These latter were made by the Horner reaction of phosphorylated carbamates 12 and 13 with the appropriate aldehydes 10 and 11

  生物碱（±）-cryptopleurine 1，（±）-antofine 2，和（±）-deoxypergularinine 3是由2- arylmethylpiperidine的的Pictet Spengler环化生成合成并-pyrrolidines 4,5和6通过顺序获得Ñ -deprotection-还原母体氨基甲酸酯7、8和9。后者是通过磷酸氨基甲酸酯12和13与适当的醛10和11的霍纳反应制得的。
• Expedient Syntheses of Antofine and Cryptopleurine via Intramolecular 1,3-Dipolar Cycloaddition
  作者：Sanghee Kim、Yun Mi Lee、Jaekwang Lee、Taeho Lee、Ye Fu、Yanling Song、Jihee Cho、Deukjoon Kim

  DOI：10.1021/jo070668x

  日期：2007.6.1

  The practical and expedient total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, antofine and cryptopleurine, are described. Construction of the pyrrolidine and piperidine ring of each alkaloid was achieved by using an intramolecular 1,3-dipolar cycloaddition of an azide onto an alkene and subsequent reduction of the resulting imine and aziridine.
• Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids
  作者：Kai-Liang Wang、Mao-Yun Lü、Qing-Min Wang、Run-Qiu Huang

  DOI：10.1016/j.tet.2008.06.003

  日期：2008.8

  Iron(III) chloride has been used to prepare polymethoxy-substituted phenanthrene-9-carboxylic acid via intramolecular oxidative coupling at room temperature in excellent yields. Mild reaction conditions and the use of environmentally friendly FeCl3 provide a novel practical route for the synthesis of the important phenanthrene ring. The further application of this protocol as the key step to total

  氯化铁（III）已用于在室温下通过分子内氧化偶合以优异的收率制备聚甲氧基取代的菲-9羧酸。温和的反应条件和使用环保的FeCl 3为重要的菲环的合成提供了一条新颖的实用途径。从易于获得的吡咯开始，分别以48％，44％和46％的总收率实现了该方案作为酪氨酸，脱氧酪氨酸和antofine全面合成关键步骤的进一步应用。这种新的高效策略具有许多优势。该实验过程在温和条件下简单，原子经济性很高，没有任何保护基，原料便宜或易于制备。因此，这种简短实用的方法适用于大规模生产。
• Synthesis and structure–activity studies of antofine analogues as potential anticancer agents
  作者：Ye Fu、Sang Kook Lee、Hye-Young Min、Taeho Lee、Jaekwang Lee、Maosheng Cheng、Sanghee Kim

  DOI：10.1016/j.bmcl.2006.09.080

  日期：2007.1

  Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.