4-bromofuran-3-carbaldehyde | 164513-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromofuran-3-carbaldehyde
• 英文别名: 3-bromofuran-4-carboxaldehyde
• CAS: 164513-46-6
• 化学式: C₅H₃BrO₂
• 分子量: 174.982
• InChiKey: YAHPWJLCYPSKEE-UHFFFAOYSA-N

物化性质

• 沸点：
  193.0±20.0 °C(Predicted)
• 密度：
  1.748±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromofuran-3-carbaldehyde 在 sodium tetrahydroborate 、 potassium tert-butylate 、 叔丁基锂 、 三溴化磷 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 4.25h， 生成 5-[2-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-1-methyl-eth-(E)-ylidene]-5,6-dihydro-cyclopenta[c]furan-4-one
  参考文献：
  名称：

  Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

  摘要：

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).

  DOI：

  10.1016/s0040-4039(00)73095-4
• 作为产物：
  描述：

  3,4-二溴呋喃 、 N,N-二甲基甲酰胺 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到4-bromofuran-3-carbaldehyde
  参考文献：
  名称：

  轻松访问新型（5 + 5）杂环杂环化合物：呋喃吡咯，咪唑咪唑和吡咯并咪唑的合成

  摘要：

  抽象的 我们描述的3-芳基-6-的合成ħ -呋喃并[2,3- b ]吡咯-5-羧酸乙酯2，5-芳基-1- ħ -咪唑并[1,2一〕咪唑3，和一个乙基-1-芳基-1,4-二氢吡咯并[2,3- d ]咪唑-5-羧酸酯4作为PI3K激酶抑制剂的新铰链结合基序。形成2和4的关键反应是丙烯酰胺的Hemmetsberger-Knittel环化反应。3的核心可通过α-卤代酮与2-氨基咪唑的反应来获得。 我们描述的3-芳基-6-的合成ħ -呋喃并[2,3- b ]吡咯-5-羧酸乙酯2，5-芳基-1- ħ -咪唑并[1,2一〕咪唑3，和一个乙基-1-芳基-1,4-二氢吡咯并[2,3- d ]咪唑-5-羧酸酯4作为PI3K激酶抑制剂的新铰链结合基序。形成2和4的关键反应是丙烯酰胺的Hemmetsberger-Knittel环化反应。3的核心可通过α-卤代酮与2-氨基咪唑的反应来获得。

  DOI：

  10.1055/s-0039-1689916

文献信息

• (Hetero)-aryl ketones derivatives with antibacterial properties
  申请人：SmithKline Beecham p.l.c.

  公开号：US05536745A1

  公开（公告）日：1996-07-16

  Conformationally restricted aryl and heteroaryl ketones derived from monic acid have useful antibacterial properties.

  通过莫尼酸衍生的构象受限芳基和杂环酮具有有用的抗菌性能。
• New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties
  作者：Sumesh Eswaran、Airody Vasudeva Adhikari、Imran H. Chowdhury、Nishith K. Pal、K.D. Thomas

  DOI：10.1016/j.ejmech.2010.04.022

  日期：2010.8

  Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence, substituted aniline was cyclized to 4-hydroxy quinoline 1, which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3, obtained from the compound 2, was successfully converted to target quinoline derivatives, viz. hydrazones 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H(37)Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid
  作者：Neil D. Pearson、Nigel J.P. Broom、Peter J. O'Hanlon

  DOI：10.1016/s0040-4039(00)73095-4

  日期：1994.5

  Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave alpha-alkylated products (5). This alkylation procedure wa surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced with the E-isomer (7). Deprotection gave the monic acid derived ketone (1).
• A Facile Access to Novel (5+5) Annellated Heterocycles: Synthesis of a Furopyrrole, an Imidazoimidazole and a Pyrroloimidazole
  作者：Pavol Zlatoidský、Elisa Martinelli、Emil Svensson、Alexis Pruvost

  DOI：10.1055/s-0039-1689916

  日期：2019.9

  We describe the synthesis of an ethyl 3-aryl-6H-furo[2,3-b]pyrrole-5-carboxylate 2, a 5-aryl-1H-imidazo[1,2-a]imidazole 3, and an ethyl-1-aryl-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate 4 as new hinge-binding motifs for PI3K kinase inhibitors. A key reaction for the formation of 2 and 4 is the Hemmetsberger–Knittel cyclization of acryloazides. The core of 3 is accessible through reaction of an

  抽象的 我们描述的3-芳基-6-的合成ħ -呋喃并[2,3- b ]吡咯-5-羧酸乙酯2，5-芳基-1- ħ -咪唑并[1,2一〕咪唑3，和一个乙基-1-芳基-1,4-二氢吡咯并[2,3- d ]咪唑-5-羧酸酯4作为PI3K激酶抑制剂的新铰链结合基序。形成2和4的关键反应是丙烯酰胺的Hemmetsberger-Knittel环化反应。3的核心可通过α-卤代酮与2-氨基咪唑的反应来获得。 我们描述的3-芳基-6-的合成ħ -呋喃并[2,3- b ]吡咯-5-羧酸乙酯2，5-芳基-1- ħ -咪唑并[1,2一〕咪唑3，和一个乙基-1-芳基-1,4-二氢吡咯并[2,3- d ]咪唑-5-羧酸酯4作为PI3K激酶抑制剂的新铰链结合基序。形成2和4的关键反应是丙烯酰胺的Hemmetsberger-Knittel环化反应。3的核心可通过α-卤代酮与2-氨基咪唑的反应来获得。