5-(2,6-dichloro-phenyl)-furan-2-carbaldehyde | 94078-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2,6-dichloro-phenyl)-furan-2-carbaldehyde
• 英文别名: 5-(2,6-dichlorophenyl)-2-furaldehyde；5-(2,6-Dichlorophenyl)furan-2-carbaldehyde
• CAS: 94078-34-9
• 化学式: C₁₁H₆Cl₂O₂
• mdl: MFCD03788952
• 分子量: 241.073
• InChiKey: ZZKLPZGLXLERDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  5-(2,6-dichloro-phenyl)-furan-2-carbaldehyde 以 正丁醇 为溶剂， 生成 7-[5-(2,5-dichlorophenyl)furan-2-yl]-10,10-dimethyl-9,10,11,12-tetrahydrobenzo[b][1,7]phenanthrolin-8(7H)-one
  参考文献：
  名称：

  呋喃系列的醛在1,7-菲咯啉衍生物的合成中

  摘要：

  通过使喹啉-5-胺与5-芳基呋喃-2-甲醛和环己烷-1,3-二酮或二甲酮缩合，合成了新的化合物10,10-二甲基-7-（5-芳基呋喃-2-基）-9 ，10,11,12-四氢苯并[ b ] [1,7]菲咯啉-8（7 H）-在位置10未被取代。

  DOI：

  10.1134/s1070428016050134
• 作为产物：
  描述：

  1-(2,6-dichloro-phenyl)-buta-2,3-dien-1-one 在 silver nitrate 、 三氯氧磷 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 5-(2,6-dichloro-phenyl)-furan-2-carbaldehyde
  参考文献：
  名称：

  金催化：苯酚合成中没有空间限制。

  摘要：

  通过金催化的苯酚合成制备了不同的二氢异吲哚-4-醇和8-羟基四氢异喹啉。研究了在呋喃原料的5位上有几个空间要求的基团的反应。研究了反应时间和催化剂对产率的影响。

  DOI：

  10.1002/chem.200600533

文献信息

• Rational design of apoptosis signal-regulating kinase 1 inhibitors: Discovering novel structural scaffold
  作者：Galyna P. Volynets、Volodymyr G. Bdzhola、Andriy G. Golub、Anatoliy R. Synyugin、Maksym A. Chekanov、Oleksandr P. Kukharenko、Sergiy M. Yarmoluk

  DOI：10.1016/j.ejmech.2012.09.022

  日期：2013.3

  Increased activity of apoptosis signal-regulating kinase 1 (ASK1) is associated with a number of human disorders and the inhibitors of ASK1 may become important compounds for pharmaceutical application. Here we report novel ASK1 inhibitor scaffold, namely 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one, that has been identified using virtual screening and biochemical tests. A series of derivatives has been synthesized and evaluated in vitro towards human protein kinase ASK1. It was revealed that the most active compounds 4-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid and 6-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)hexanoic acid inhibit ASK1 with IC50 of 0.2 mu M. Structure activity relationships of 33 derivatives of 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one have been studied and binding mode of this chemical class has been predicted. (C) 2012 Elsevier Masson SAS. All rights reserved.
• JANDA, L.;VOTICKY, Z., CHEM. ZVESTI, 1984, 38, N 4, 507-513
  作者：JANDA, L.、VOTICKY, Z.

  DOI：——

  日期：——
• Gold Catalysis: No Steric Limitations in the Phenol Synthesis
  作者：A. Stephen K. Hashmi、Ralph Salathé、Wolfgang Frey

  DOI：10.1002/chem.200600533

  日期：2006.9.6

  Different dihydroisoindol-4-ols and 8-hydroxytetrahydroisoquinolines were prepared by the gold-catalyzed phenol synthesis. The reaction was investigated with several sterically demanding groups in the 5-position of the furan starting material. The influence of the reaction time and the catalyst on the yield was investigated.

  通过金催化的苯酚合成制备了不同的二氢异吲哚-4-醇和8-羟基四氢异喹啉。研究了在呋喃原料的5位上有几个空间要求的基团的反应。研究了反应时间和催化剂对产率的影响。
• Aldehydes of furan series in the synthesis of 1,7-phenanthroline derivatives
  作者：N. G. Kozlov、A. B. Tereshko

  DOI：10.1134/s1070428016050134

  日期：2016.5

  By condensation of quinolin-5-amine with 5-arylfuran-2-carbaldehydes and cyclohexane-1,3-dione or dimedone new compounds were synthesized, 10,10-dimethyl-7-(5-arylfuran-2-yl)-9,10,11,12-tetrahydrobenzo[b][1,7]phenanthrolin-8(7H)-ones unsubstituted in the position 10.

  通过使喹啉-5-胺与5-芳基呋喃-2-甲醛和环己烷-1,3-二酮或二甲酮缩合，合成了新的化合物10,10-二甲基-7-（5-芳基呋喃-2-基）-9 ，10,11,12-四氢苯并[ b ] [1,7]菲咯啉-8（7 H）-在位置10未被取代。