1-(3,4-二甲氧基苯基)-2-吡咯烷-2-基乙酮 | 60890-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,4-二甲氧基苯基)-2-吡咯烷-2-基乙酮
• 英文名称: ruspolinone
• 英文别名: 1-(3,4-dimethoxyphenyl)-2-pyrrolidin-2-ylethanone
• CAS: 60890-27-9
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD22704845
• 分子量: 249.31
• InChiKey: TYXKSMFICLVQCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(3,4-二甲氧基苯基)-2-吡咯烷-2-基乙酮 在 氢氧化钾 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 6,7-bis(3,4-dimethoxyphenyl)-2,3,8,8a-tetrahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents

  摘要：

  A series of 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues were synthesized and evaluated for cytotoxic activity against eight human cancer cell lines. Compounds 18, 21, 28, 29, 30 and 31 showed cytotoxic activity with GI(50) values in the range of 2.1-8.1 muM concentration. Among these, compounds 21 and 28 exhibited good pharmacokinetic properties. These compounds were further evaluated for their in vivo efficacy in modified hollow fibre assay (HFA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00263-4
• 作为产物：
  描述：

  2-<2-(3,4-dimethoxyphenyl)-2-oxoethyl>1-pyrrolidinecarboxaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.25h， 以80%的产率得到1-(3,4-二甲氧基苯基)-2-吡咯烷-2-基乙酮
  参考文献：
  名称：

  2-苯基磺酰基-哌啶和-吡咯烷与碳亲核试剂的取代反应：吡咯烷生物碱去甲茶氨酸和ruspolinone的合成

  摘要：

  通过用苯磺酸进行处理，由相应的N-酰基氨基缩醛制备几种2-苯基磺酰基-哌啶和-吡咯烷。在与各种碳亲核试剂反应时，这些砜产生了良好的取代产物收率。这些研究中使用的典型亲核试剂是衍生自Grignard试剂的有机金属试剂和卤化锌，以及在路易斯酸存在下的甲硅烷基烯醇醚，甲硅烷基烯酮缩醛，烯丙基硅烷和三甲基甲硅烷基氰化物。这些方法被用于合成两种天然产物生物碱。去甲去氧肾上腺素（38）和Ruspolinone（40）。

  DOI：

  10.1016/s0040-4020(01)86388-2

文献信息

• Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone
  作者：A. Couture、E. Deniau、P. Grandclaudon、S. Lebrun

  DOI：10.1016/0040-4039(96)01765-0

  日期：1996.10

  Upon irradiation in neutral solvent, the diversely substituted 1-aroyl-2-methylenepiperidines 6a-f give rise to photocyclized products 4a-f while their pyrrolidine congeners 7a,c,d afford enaminoketones 18a,c,d products of photo-Fries rearrangement.

  在中性溶剂中辐照后，被不同取代的1-芳酰基-2-亚甲基哌啶6a-f产生光环化产物4a-f，而它们的吡咯烷同类物7a，c，得到光-弗里斯重排的烯氨基酮18a，c，d产物。
• Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction
  作者：James L. Galman、Iustina Slabu、Fabio Parmeggiani、Nicholas J. Turner

  DOI：10.1039/c8cc06759g

  日期：——

  moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.

  基于哌啶和吡咯烷的杂环是天然产物和药物活性分子中的关键部分。报道了一种基于脂肪酶与 α,ω-二胺转氨酶组合的新型多酶方法，开辟了广泛的 2-取代 N-杂环生物碱的合成、分离和表征。
• Biomimetic Approach toward the Total Synthesis of <i>rac</i>-2-(Acylmethylene)pyrrolidine Alkaloids
  作者：Yu-Chiao Shih、Pei-Hua Tsai、Chia-Chun Hsu、Chih-Wei Chang、Yuandong Jhong、Yun-Chung Chen、Tun-Cheng Chien

  DOI：10.1021/acs.joc.5b00836

  日期：2015.7.2

  intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.

  2-（Acylmethylene）吡咯烷衍生物通过从各种甲基酮和1-烷基-1- pyrroliniums，生成分子间decarbonylative曼尼希反应合成原位由1- alkylprolines。该方法模拟了生物合成途径，并提供了直接接触一系列2-（酰基亚甲基）吡咯烷生物碱的方法，包括hy，N-甲基ruspolinone，dehydrodarlinine和ruspolinone。
• Total synthesis of the tylophora alkaloids rusplinone, 13aα-secoantofine, and antofine using a multicatalytic oxidative aminochlorocarbonylation/Friedel–Crafts reaction
  作者：Lisa M. Ambrosini、Tim A. Cernak、Tristan H. Lambert

  DOI：10.1016/j.tet.2010.03.021

  日期：2010.6

  A rapid synthetic approach to the tylophora alkaloids antofine and 13aα-secoantofine is presented that makes use of a multicatalytic oxidative aminochlorocarbonylation/Friedel–Crafts reaction as the key step. This reaction, along with a one-pot, three-step telescoped process offers a three or four-pot sequence to access the title compounds in high overall yield.

  提出了一种快速合成tylophora生物碱antofine和13aα-secoantofine的方法，该方法利用了多催化氧化氨基氯羰基化/ Friedel-Crafts反应作为关键步骤。该反应以及一锅，三步伸缩过程提供了三锅或四锅顺序，可以高总收率获得标题化合物。
• Biosynthesis of tylophorine and tylophorinine
  作者：Dewan S. Bhakuni、Virendra K. Mangla

  DOI：10.1016/s0040-4020(01)92028-9

  日期：1981.1

  Administration of 3,4-dihydroxyphenyl[2-14C]alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7 of tylophorine and tylophorinine [phenanthroin dolizidine alkaloids] are derived from dopa. Tracer experiments with 6,7-diphenylhexahydroindolizines (1-7) and (26) demonstrated that compound 1 is efficiently and specifically incorporated into tylophorine (13) and tylophorinine (16). Compounds (3), (4) and (26) were not metabolized by the plants to form (13) and (16) whereas (5) and (6) were utilized to yield (13) and (16). Compound (2) was very poorly converted into (13) and (16) and thus is not on the major biosynthetic pathway of (13) and (16).