4,4'-(2,5-呋喃二基)二-苯甲腈 | 55368-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 4,4'-(2,5-呋喃二基)二-苯甲腈
• 中文别名: 4,4-(2,5-呋喃二基)双-苯甲腈
• 英文名称: 4,4’-(furan-2,5-diyl)dibenzonitrile
• 英文别名: 4,4′-(furan-2,5-diyl)dibenzonitrile；2,5-bis-(4-cyanophenyl)furan；2,5-bis(4-cyanophenyl)furan；2,5-di(4-cyanophenyl)furan；4,4'-furan-2,5-diyl-bis-benzonitrile；4-[5-(4-cyanophenyl)furan-2-yl]benzonitrile
• CAS: 55368-37-1
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: JVFLSYUMYIPFBA-UHFFFAOYSA-N

物化性质

• 熔点：
  >250°C
• 溶解度：
  可溶于氯仿（轻微、加热、超声处理）、甲醇（轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-(2,5-呋喃二基)二-苯甲腈 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以75%的产率得到2,5-bis(4-carboxyphenyl)furan
  参考文献：
  名称：

  2,5-Bis[4-(N-alkylamidino)phenyl]furans as Anti-Pneumocystis carinii Agents

  摘要：

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.

  DOI：

  10.1021/jm970570i
• 作为产物：
  描述：

  对氰基苯乙酮 在 盐酸 、 乙醇 、 六氟异丙醇 、 三乙胺 、 zinc(II) chloride 作用下， 以 水 、 甲苯 为溶剂， 反应 170.0h， 生成 4,4'-(2,5-呋喃二基)二-苯甲腈
  参考文献：
  名称：

  六氟异丙醇作为溶剂和促进剂在Paal-Knorr合成N-取代的二芳基吡咯中

  摘要：

  据报道，通过Paal-Knorr吡咯合成方法，由通常难溶的相应1,4-二酮可无添​​加剂合成具有挑战性的N-取代的芳基吡咯，该方法利用了1,1,1,3的独特性质，3,3-六氟异丙醇（HFIP）作为溶剂和反应促进剂。我们的程序提供了简单的执行和纯化方法，以及易于放大的规模，可用于Paal-Knorr合成中，结构复杂的许多吡咯，包括中等难度到极高产率的具有挑战性的四和五取代的吡咯。HFIP也可以用作呋喃和噻吩的Paal-Knorr合成中的溶剂。然而，在吡咯的合成中，溶剂作用更为明显。

  DOI：

  10.1016/j.tet.2021.131985

文献信息

• Methyl 2-Furoate: An Alternative Reagent to Furan for Palladium-Catalysed Direct Arylation
  作者：Hai Yan Fu、Henri Doucet

  DOI：10.1002/ejoc.201101102

  日期：2011.12

  The palladium-catalysed direct arylation of methyl 2-furoate with aryl bromides was studied. The use of KOAc as the base, dimethylacetamide (DMAc) as the solvent and Pd(OAc)2 as the catalyst was found to give 5-arylfurans regioselectively and without decarboxylation. These methyl 5-aryl-2-furoates gave 2,5-diarylfurans by decarboxylative coupling by using Pd(OAc)2 as the catalyst. Methyl 2-furoate

  研究了钯催化的 2-糠酸甲酯与芳基溴化物的直接芳基化反应。发现使用 KOAc 作为碱、二甲基乙酰胺 (DMAc) 作为溶剂和 Pd(OAc) 2 作为催化剂可以区域选择性地得到 5-芳基呋喃并且没有脱羧。这些5-芳基-2-糠酸甲酯通过使用Pd(OAc) 2 作为催化剂的脱羧偶联得到2,5-二芳基呋喃。因此，2-糠酸甲酯代表了一种方便的替代呋喃的底物，用于合成单或多芳基化呋喃。
• Small molecule inhibition of RNA/ligand binding
  申请人：University of Massachusetts Medical Center

  公开号：US05935776A1

  公开（公告）日：1999-08-10

  Disclosed is a method for the inhibition of binding of a ligand to an RNA, the inhibition being mediated by a small organic molecule that binds to the RNA, thereby inhibiting ligand binding. A preferred class of small organic molecules are compounds exemplified by 2,5-Bis\x9b4-(2-N,N-dimethylaminopropylamidino)phenyl!furan.

  揭示了一种抑制配体与RNA结合的方法，该抑制是由结合到RNA的小有机分子介导的，从而抑制配体的结合。一种首选的小有机分子类别是由2,5-双\x9b4-(2-N,N-二甲基氨丙基胺基)苯基!呋喃等化合物所示范。
• Deprotonative Metalation of Substituted Benzenes and Heteroaromatics Using Amino/Alkyl Mixed Lithium-Zinc Combinations
  作者：Katia Snégaroff、Shinsuke Komagawa、Floris Chevallier、Philippe C. Gros、Stéphane Golhen、Thierry Roisnel、Masanobu Uchiyama、Florence Mongin

  DOI：10.1002/chem.201000543

  日期：2010.7.19

  Different homoleptic and heteroleptic lithium–zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations. In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures. The best basic mixtures were obtained either by combining ZnCl2⋅TMEDA (TMEDA=N,N,N′,N′‐tetramethylethylenediamine)

  制备了不同的均溶和异溶锂-锌组合，并根据NMR光谱实验和DFT计算获得了结构元素。考虑到它们使苯甲醚金属化的能力，提出了一些途径以证明对某些混合物观察到的协同作用是正确的。通过结合ZnCl 2 · TMEDA（TMEDA = N，N，N'，N'-四甲基乙二胺）（[TMp = 2,2,6,6-四甲基哌啶子基; 3当量）或通过用烷基取代先有混合物中的TMp之一。接下来研究了据推测形成的芳香族锌酸锂的反应性，并证明其与底物，碱和亲电试剂有关。芳族锌酸锂最终参与了钯与芳族氯化物和溴化物的交叉偶联反应。
• Novel prodrugs for antimicrobial amidines
  申请人：——

  公开号：US20020019437A1

  公开（公告）日：2002-02-14

  A methods of treating an infection comprises administering a therapeutically effective amount of a compound described by the Formula (I): 1 wherein: X may be O, S, or NR′ wherein R′ is H or loweralkyl; R 1 and R 2 may be independently selected from the group consisting of H, loweralkyl, oxyalkyl, alkoxyalkyl, cycloalkyl, aryl, hydroxyalkyl, aminoalkyl, and alkylaminoalkyl; R 3 and R 4 are each independently selected from the group consisting of H, loweralkyl, halogen, oxyalkyl, oxyaryl, and oxyarylalkyl; R 5 is represented by a formula selected from the group consisting of: 2 wherein: X 1 , X 2 , and X 3 are independently selected from O and S; and R 6 and R 7 are independently selected from the group consisting of loweralkyl, aryl, alkylaryl, oxyaryl, an ester-containing substituent, and oxyalkyl; or a pharmaceutically acceptable salt thereof.

  一种治疗感染的方法包括给予公式（I）描述的化合物的治疗有效量：其中：X可以是O、S或NR′，其中R′为H或较低烷基；R1和R2可以独立地选择自H、较低烷基、氧烷基、烷氧基烷基、环烷基、芳基、羟基烷基、氨基烷基和烷基氨基烷基的群；R3和R4各自独立地选择自H、较低烷基、卤素、氧烷基、氧芳基和氧芳基烷基的群；R5由以下公式中选择：其中：X1、X2和X3独立选择自O和S；R6和R7独立选择自较低烷基、芳基、烷基芳基、氧芳基、含酯基取代基和氧烷基的群；或其药学上可接受的盐。
• Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans
  作者：Bijan P. Das、David W. Boykin

  DOI：10.1021/jm00214a014

  日期：1977.4

  Eighteen substituted 2,5-bis(4-guanylphenyl)furans and related analogues, including "masked" amidines in which the guanyl function is incorporated into a heterocyclic ring, have been synthesized and their antimalarial and antitrypanosomal activity has been evaluated. None of the compounds exhibited high orders of antimalarial activity; however, 11 were very active against Trypanosoma rhodesiense in

  已经合成了十八个取代的2，5-双（4-胍基苯基）呋喃和相关类似物，包括其中将胍基功能结合到杂环中的“掩蔽的” am，并且已经评估了它们的抗疟和抗锥虫活性。这些化合物均未显示出高水平的抗疟活性。但是，有11种在小鼠中对罗氏锥虫有很高的活性。六种化合物，包括2,5-双（4-胍基苯基）呋喃（4）及其3-氯（32），3,4-二氯（31），3-甲基（25），3,4-二甲基（20 ）和3-氯-4-甲基（38）衍生物在小鼠体内以亚毫克剂量水平产生治愈作用; 3,4-二甲基（20）类似物表现出延长的治疗效果，单次给药后可提供30天的保护，以抵抗罗德氏梭菌的攻击。这六个化合物在该筛选中的活性比stilbamidine，hydroxystilbamidine和pentamidine更高。通常，“被掩盖的” am比其真正的鸟嘌呤对应物显示出更低的抗胰蛋白酶活性。由1,4-二-对溴苯基-1,4-丁二酮经环脱水呋喃合成2