3-乙基-4,5-二甲基-1H-吡咯-2-甲醛 | 97336-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙基-4,5-二甲基-1H-吡咯-2-甲醛
• 英文名称: 3-ethyl-4,5-dimethyl-pyrrole-2-carbaldehyde
• 英文别名: 3-Aethyl-4,5-dimethyl-pyrrol-2-carbaldehyd；3-Ethyl-4,5-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 97336-42-0
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: INRLLMQZKREWLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-乙基-4,5-二甲基-1H-吡咯-2-甲醛 在 硫酸 、 氢溴酸 、 溶剂黄146 、 三氟乙酸 、 copper dichloride 作用下， 反应 5.42h， 生成 12,13-butano-3,8,17-triethyl-2,17,18-trimethylporphyrin
  参考文献：
  名称：

  Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles

  摘要：

  Benzo- and tetrahydrobenzoporphyrins are widespread constituents of oil shales and petroleum. Although the origins of these materials are not known, a case is made for divinylchlorophyll a, a widespread pigment in marine algae, being the precursor to many of these geoporphyrins. Total syntheses of four tetrahydrobenzoporphyrins related to etioporphyrin III are described. Tetrahydroisoindoles were prepared by condensation of isocyanoacetates with 1-nitrocyclohexene in the presence of DBU or by reaction of aminomalonates with 2-formylcyclohexanone. Condensation of 3-unsubstituted 4,5,6,7-tetrahydro-2H-isoindoles 23c and 23d with (acetoxymethyl)pyrroles in the presence of Montmorillonite clay gave dipyrrylmethanes 28a and 36a in excellent yield. Hydrogenolysis of the benzyl esters and subsequent acid-catalyzed condensation with pyrrole aldehydes 37a and/or 37b gave a series of a,c-biladiene dihydrobromides. Copper(II) mediated cyclization of the a,c-biladienes 32, 33, 35, and 38, followed by demetallation with 15% sulfuric acid-trifluoroacetic acid, gave four isomeric tetrahydrobenzoporphyrins 10-13 in unusually high yield. This work provides a general route for the synthesis of these important porphyrin molecular fossils.

  DOI：

  10.1021/jo00044a013
• 作为产物：
  描述：

  benzyl 3-ethyl-4,5-dimethyl-pyrrole-2-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 为溶剂， -78.0~102.0 ℃ 、2.93 kPa 条件下， 反应 2.0h， 生成 3-乙基-4,5-二甲基-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Clezy, Peter S.; Fookes, Christopher J. R.; Prashar, Jognandan K., Australian Journal of Chemistry, 1989, vol. 42, # 6, p. 775 - 786

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluations of 3-Substituted Indolin-2-ones:  A Novel Class of Tyrosine Kinase Inhibitors That Exhibit Selectivity toward Particular Receptor Tyrosine Kinases
  作者：Li Sun、Ngoc Tran、Flora Tang、Harald App、Peter Hirth、Gerald McMahon、Cho Tang

  DOI：10.1021/jm980123i

  日期：1998.7.1

  analysis for these compounds and their relative potency and selectivity to inhibit particular RTKs has determined that (1) 3-[(five-membered heteroaryl ring)methylidenyl]indolin-2-ones are highly specific against the VEGF (Flk-1) RTK activity, (2) 3-(substituted benzylidenyl)indolin-2-ones containing bulky group(s) in the phenyl ring at the C-3 position of indolin-2-ones showed high selectivity toward

  已经设计并合成了3-取代的吲哚-2-酮，作为一类新型的酪氨酸激酶抑制剂，该抑制剂对不同的受体酪氨酸激酶（RTK）具有选择性。已经评估了这些化合物对完整细胞中一组RTK的相对抑制特性。通过修饰3-取代的吲哚-2-酮，我们鉴定了在亚微摩尔水平下显示选择性抑制各种RTK的配体依赖性自磷酸化的化合物。这些化合物的结构活性分析及其抑制特定RTK的相对效能和选择性已确定（1）3-[（（五元杂芳基环）亚甲基]茚满-2-酮对VEGF（Flk-1 ）RTK活动，（2）在吲哚-2-酮的C-3位的C-3位置的苯环中含有庞大基团的3-（取代的苄基）吲哚啉-2-酮显示出对EGF和Her-2 RTK的高选择性，并且（ 3）在针对PDGF和VEGF（Flk-1）RTK进行测试时，在吲哚-2-酮（16）的C-3位置包含延伸的侧链的化合物表现出较高的效价和选择性。这些3-取代的吲哚-2-酮中的两个的最近公布的晶体学数据提供
• Porphyrins with exocyclic rings. Part 3. A reassessment on the utility of cyclopenta[b]pyrroles in the synthesis of porphyrin molecular fossils. Preparation of three type II porphyrins related to deoxophylloerythroetioporphyrin (DPEP).
  作者：Timothy D. Lash、James J. Catarello

  DOI：10.1016/s0040-4020(01)85734-3

  日期：1993.1

  cyclopenta[b]pyrroles in porphyrin synthesis has been reinvestigated. A 6-oxocyclopenta[b]pyrrole 18 was prepared by cyclization of the propanoyl chloride sidechain of an α-unsubstituted pyrrole 17d in the presence of tin(IV) chloride. Subsequent reduction with sodium borohydride afforded the corresponding 6-hydroxy compound 10 and further acid catalyzed condensation with α-unsubstituted pyrroles 11a and

  环戊并[b]吡咯在卟啉合成中的效用已被重新研究。通过在氯化锡（IV）存在下将α-未取代的吡咯17d的丙酰氯侧链环化来制备6-氧代环戊[b]吡咯18。随后用硼氢化钠还原得到相应的6-羟基化合物10，并与α-未取代的吡咯11a和11b进行进一步的酸催化缩合，以优异的产率得到了新型的6-吡咯基环戊[b]吡咯22a和22b。尝试制备脱氧叶绿素铁卟啉（DPEP; 2），这是一种广泛的沉积卟啉分子化石，使用三茂铁-a，c-比拉二烯路线从这些二吡咯中间体得到的结果是不成功的。然而，使用麦克唐纳缩合法成功地进行了三种相关的内消旋β-乙基卟啉的合成，收率中等至良好。在中间开链四吡咯的环戊烯环稠合位点保留sp 3杂化碳桥在大环形成过程中似乎至关重要，因为这会减少外围取代基和碳环之间的空间排斥。
• Total synthesis of the C31 and C32 15,17-butanoporphyrins from oil shales
  作者：Timothy D. Lash、Marty C. Johnson

  DOI：10.1016/s0040-4039(00)76173-9

  日期：1989.1

  Copper(II) promoted cyclizations of a,c-biladienes incorporating seven-membered carbocyclic rings gave poor yields of porphyrins; however, superior yields of petroporphyrins and were obtained when cyclizations were mediated by silver iodate-zinc acetate.

  铜（II）促进了结合有七元碳环的α，c-胆二烯的环化，卟啉的收率很低；然而，petroporphyrins的优越的产率和时的环化反应是由乙酸银，碘酸-锌介导的获得。
• [EN] METAL COMPLEXES AND FLUORINATION THEREOF<br/>[FR] COMPLEXES MÉTALLIQUES ET LEUR FLUORATION
  申请人：GE HEALTHCARE LTD

  公开号：WO2014177689A1

  公开（公告）日：2014-11-06

  The present invention relates to a method of labelling biological molecules with 18F, via attachment of fluorine to a metal complex, where the metal complex is conjugated to the biological molecule. The invention highlights the incorporation of hydrogen bonding (H-bonding) into the metal complex scaffold, and how this can be utilised to improve the kinetics of fluoride incorporation. Also provided are pharmaceutical compositions, kits and methods of in vivo imaging.

  本发明涉及一种使用18F标记生物分子的方法，通过将氟附着在金属配合物上，其中金属配合物与生物分子结合。该发明突出了将氢键（H键）结合到金属配合物支架中，以及如何利用这一特性来改善氟化物的结合动力学。同时提供了用于体内成像的药物组合物、试剂盒和方法。
• METAL COMPLEXES AND FLUORINATION THEREOF
  申请人：GE HEALTHCARE LIMITED

  公开号：US20160082136A1

  公开（公告）日：2016-03-24

  A method of labelling biological molecules with 18 F, via attachment of fluorine to a metal complex, where the metal complex is conjugated to the biological molecule. The invention highlights the incorporation of hydrogen bonding (H-bonding) into the metal complex scaffold, and how this can be utilised to improve the kinetics of fluoride incorporation. Also provided are pharmaceutical compositions, kits and methods of in vivo imaging.

  一种使用18F标记生物分子的方法，通过将氟附加到金属配合物上，其中金属配合物与生物分子共轭。该发明强调将氢键(H-bonding)纳入金属配合物支架中，以及如何利用它来改善氟化物结合动力学。还提供了制药组合物、工具箱和体内成像方法。