2,5-dimethylthiophene-3,4-dicarboxaldehyde | 5368-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dimethylthiophene-3,4-dicarboxaldehyde
• 英文别名: 2,5-dimethylthiophene-3,4-dicarbaldehyde；3,4-diformyl-2,5-dimethylthiophen；2,5-dimethyl-thiophene-3,4-dicarbaldehyde；2,5-Dimethyl-3,4-thiophen-dialdehyd；2,5-Dimethyl-thiophen-dialdehyd
• CAS: 5368-72-9
• 化学式: C₈H₈O₂S
• mdl: MFCD01859990
• 分子量: 168.216
• InChiKey: JKYJVVJLFDVLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dimethylthiophene-3,4-dicarboxaldehyde 在 palladium on activated charcoal 吡啶 、 potassium tert-butylate 、 氢气 、 sodium ethanolate 、 copper diacetate 作用下， 以 甲醇 、 乙醚 、 叔丁醇 、 苯 为溶剂， 反应 73.0h， 生成 15,17-dimethyl-16-thiabicyclo<12.3.0>heptadeca-14,17-diene
  参考文献：
  名称：

  Brown, Trevor M.; Carruthers, William; Pellatt, Martin G., Journal of the Chemical Society. Perkin transactions I, 1982, p. 483 - 487

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-bis(bromomethyl)-2,5-dimethylthiophene 在 2-硝基丙烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以74%的产率得到2,5-dimethylthiophene-3,4-dicarboxaldehyde
  参考文献：
  名称：

  Synthesis of N-protected indolaldehydes using modified Hass procedure

  摘要：

  A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.035

文献信息

• Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
  作者：Radhakrishnan Sureshbabu、Velu Saravanan、Vasudevan Dhayalan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201001309

  日期：2011.2

  ]-fused carbazoles has been developed startingfrom suitably substituted 2/3-(bromomethyl)indoles and ar-enes under Lewis acid catalysis. The attractive feature ofthis protocol is the fact that a wide variety of π-conjugatedannulated carbazoles can be readily accessed by the appro-priate choice of arenes and heteroarenes. The annulationprotocol has been extended to (bromomethyl)benzene aswell as 2,

  在路易斯酸催化下，以适当取代的 2/3-（溴甲基）吲哚和芳烯为原料开发了]-稠合咔唑。本协议的有吸引力的特征是，可以通过竞争和杂种丁烯的应用选择可以容易地访问各种π缀合的咔唑。环化协议已扩展到（溴甲基）苯以及 2,5-双（溴甲基）噻吩。发现吲哚基-2-甲基乙酸酯的环化不如相应的2-(溴甲基)吲哚合适。然而，在苄体系的情况下，发现相应的醋酸盐更适用。在这项工作中开发的路易斯酸介导的级联环化序列可能会导致在多环芳香杂环领域的新应用。
• The synthesis, characterization, and structure of a series of 4<i>H</i>-thieno[3,4-<i>c</i>]pyrroles and their corresponding pyrrolium cyanoborohydride salts
  作者：Nathan C. Tice、Sarah M. Peak、Benjamin T. Cannon、Ethan S. Laha、Eli G. Estes、Chad A. Snyder、Sean Parkin

  DOI：10.1080/17415993.2014.933340

  日期：2014.11.2

  6-dihydro-4H-thieno[3,4-c]pyrroles was accomplished by the reductive amination of 2,5-dimethylthiophene-3,4-dicarbaldehyde with various primary amines in a solution of sodium cyanoborohydride and methanol/acetic acid (80–88% yield). For the N-alkyl cases, the product isolated was the cyanoborohydride salt of the desired product, 1,3-dimethyl-5-alkyl-5,6-dihydro-4H-thieno[3,4-c]-5-pyrrolium cyanoborohydride

  N-取代的 5,6-二氢-4H-噻吩并[3,4-c]吡咯的一般方便途径是通过 2,5-二甲基噻吩-3,4-二甲醛与各种伯胺在氰基硼氢化钠和甲醇/乙酸的溶液（产率 80-88%）。对于 N-烷基情况，分离的产物是所需产物 1,3-二甲基-5-烷基-5,6-二氢-4H-噻吩并[3,4-c]-5-吡咯鎓氰基硼氢化物的盐. 对于使用苯胺的芳基情况，分离出所需的游离吡咯、1,3-二甲基-5-苯基-5,6-二氢-4H-噻吩并[3,4-c]吡咯。N-丙基和 N-苯基试验的 X 射线晶体学分析证实了产物的盐和游离胺性质。图形概要
• Synthesis and diels-alder reaction of thieno[2,3-c:4,5-c']dipyrroles
  作者：Chin-Kang Sha、Chiu-Peng Tsou

  DOI：10.1016/s0040-4020(01)80426-9

  日期：1993.7

  An efficient method for the synthesis of the thieno[2,3-c:4,5-c']dipyrrole ring system is described. Reaction of 13 with sodium azide followed by the treatment with triphenylphosphine and water gave parent compound 4. Reaction of 13 with benzylamine or aniline afforded N,N'-disubstituted derivatives 15 and 16 respectively. Diels-Alder reaction of 15 with DMAD gave cycloadducts 17 and 18. Oxidative

  描述了一种合成噻吩并[2,3- c：4,5- c ']双吡咯环系统的有效方法。13与叠氮化钠反应，然后用三苯膦和水处理，得到母体化合物4。13与苄胺或苯胺的反应分别得到N，N′-二取代的衍生物15和16。15与DMAD的Diels-Alder反应产生环加合物17和18。从17和18氧化去除亚胺桥得到二苯并噻吩19。
• Synthesis and Structure of 5,7-Dimethylthieno[3,4-d]pyridazine
  作者：Nathan C. Tice、Sarah M. Peak、Sean Parkin

  DOI：10.3987/com-10-11940

  日期：——

  The reaction of 2,5-dimethylthiophene-3,4-dicarboxaldehye (3) with excess hydrazine hydrate afforded the desired 5,6-fused ring thiophene derivative, 5,7-dimethylthieno[3,4-d]pyridazine (4), in high yield (82%). Pyridazine 4 was characterized spectroscopically and its structure was confirmed by X-ray crystallography. Compound 4 was observed to have an inverted, coplanar stacking arrangement in the solid state.
• Synthesis of substituted carbazoles via electrocyclization of in situ generated enamines from 1-phenylsulfonyl-2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA
  作者：Radhakrishnan Sureshbabu、Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2009.03.010

  日期：2009.5

  Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF center dot DMA/DMA center dot DMA at 110 degrees C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization afforded substituted carbazoles. (C) 2009 Elsevier Ltd. All rights reserved.