4'-甲酰基-3-联苯甲腈 | 230647-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4'-甲酰基-3-联苯甲腈
• 英文名称: 4'-formyl-[1,1'-biphenyl]-3-carbonitrile
• 英文别名: 4'-Formyl-biphenyl-3-carbonitrile；3-(4-formylphenyl)benzonitrile
• CAS: 230647-84-4
• 化学式: C₁₄H₉NO
• 分子量: 207.232
• InChiKey: WIBFCEQQNYPLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-甲酰基-3-联苯甲腈 在 盐酸羟胺 、 potassium tert-butylate 、 sodium hydrogensulfite 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3'-(N-hydroxyamidino)biphenyl-4-yl]-1H-benzimidazole-5-N-hydroxyamidine
  参考文献：
  名称：

  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

  摘要：

  A series of near-linear biphenyl benzimidazole diamidines 5a-h were synthesized from their respective diamidoximes (4a-h), through the bis-O-acetoxyamidoxime, followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. Compounds 4a-h were obtained in three steps, starting with the Suzuki coupling reaction of the appropriate haloarylcarbonitriles la-g or 4-bromo-2-fluorobenzaldehyde with 4-formylphenylboronic acid or 4-cyanophenylboronic acid to form the anticipated 4-formylbiphenyl carbonitrile analogues 2a-h. Subsequent condensation of the formyl derivatives 2a-h with 3,4-diaminobenzonitrile in the presence of sodium bisulfite or 1,4-benzoquinone gave the desired dinitriles 3a-h, the precursors for 4a-h. All the diamidines showed strong DNA affinities, as judged by high Delta T-m values with poly(dA.dT)(2). The compounds were quite active in vitro versus Trypanosoma brucei rhodesiense, giving IC50 values ranging from 3 to 37 nM. These compounds were even more active versus Plasmodium falciparum, exhibiting IC50 values ranging from 0.5 to 23 nM. The compounds showed moderate to good activity in vivo in the STIB900 model for acute African trypanosomiasis. The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.024
• 作为产物：
  描述：

  间溴苯甲腈 、 4-甲酰基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 以91%的产率得到4'-甲酰基-3-联苯甲腈
  参考文献：
  名称：

  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents

  摘要：

  A series of near-linear biphenyl benzimidazole diamidines 5a-h were synthesized from their respective diamidoximes (4a-h), through the bis-O-acetoxyamidoxime, followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. Compounds 4a-h were obtained in three steps, starting with the Suzuki coupling reaction of the appropriate haloarylcarbonitriles la-g or 4-bromo-2-fluorobenzaldehyde with 4-formylphenylboronic acid or 4-cyanophenylboronic acid to form the anticipated 4-formylbiphenyl carbonitrile analogues 2a-h. Subsequent condensation of the formyl derivatives 2a-h with 3,4-diaminobenzonitrile in the presence of sodium bisulfite or 1,4-benzoquinone gave the desired dinitriles 3a-h, the precursors for 4a-h. All the diamidines showed strong DNA affinities, as judged by high Delta T-m values with poly(dA.dT)(2). The compounds were quite active in vitro versus Trypanosoma brucei rhodesiense, giving IC50 values ranging from 3 to 37 nM. These compounds were even more active versus Plasmodium falciparum, exhibiting IC50 values ranging from 0.5 to 23 nM. The compounds showed moderate to good activity in vivo in the STIB900 model for acute African trypanosomiasis. The most active compounds 5b and e gave 3/4 cures on an IP dosage of 20 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.024

文献信息

• [EN] 4-BIARYLYL-1-PHENYLAZETIDIN-2-ONES<br/>[FR] 4-BIARYLYL-1-PHÉNYLAZÉTIDIN-2-ONES
  申请人：MICROBIA INC

  公开号：WO2005047248A1

  公开（公告）日：2005-05-26

  4-Biarylyl-1-phenylazetidin-2-ones useful for the treatment of hypercholesterolemia are disclosed. The compounds are of a general formula (I) in which formula (II) represents an aryl or heteroaryl residue, Ar represents an aryl residue; U is a two to six atom chain; and the R’s represent substituents.

  4-双苯基-1-苯基氮杂环丁烷-2-酮，用于治疗高胆固醇血症的化合物被披露。这些化合物具有通用公式(I)，其中公式(II)代表一个芳基或杂芳基残基，Ar代表一个芳基残基；U是2到6个原子的链；而R's代表取代基。
• Palladium-Catalyzed Late-Stage Direct Arene Cyanation
  作者：Da Zhao、Peng Xu、Tobias Ritter

  DOI：10.1016/j.chempr.2018.09.027

  日期：2019.1

  Methods for direct benzonitrile synthesis are sparse, despite the versatility of cyano groups in organic synthesis and the importance of benzonitriles for the dye, agrochemical, and pharmaceutical industries. We report the first general late-stage aryl C–H cyanation with broad substrate scope and functional-group tolerance. The reaction is enabled by a dual-ligand combination of quinoxaline and an

  尽管氰基在有机合成中具有多功能性，并且苯甲腈在染料，农业化学和制药行业中的重要性，但直接合成苯甲腈的方法仍然很少。我们报告了第一个一般的晚期芳基C–H氰化反应，具有较宽的底物范围和官能团耐受性。喹喔啉和氨基酸衍生的配体的双配体结合使反应得以实现。该方法适用于几种市售的小分子药物，常用药效团和有机染料的直接氰化。
• Coupling catalyst and process using the same
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20030162950A1

  公开（公告）日：2003-08-28

  There are disclosed a process for producing a coupling compound of formula (1): (Y—) (n-1) R 1 —R 2 —(R 1 ) (n′-1) (1), wherein R 1 and R 2 independently represent a substituted or unsubstituted aryl group, which process is characterized by reacting an unsaturated organic compound of formula (2): n ′(R 1 X 1 n )  (2) wherein n, n′, and R 1 are the same as defined above, and X 1 is the same or different and independently represents a leaving group and bonded with a sp2 carbon atom of R 1 group, with a boron compound of formula (3): m {R 2 (BX 2 2 ) n′ }  (3) wherein R 2 and n′ are the same as defined above, X 2 represents a hydroxy group, an alkoxy group, in the presence of a catalyst containing (A) a nickel compound, and (B) a nitrogen-containing cyclic compound, and the catalyst.

  揭示了一种制备公式(1)的偶联化合物的方法：(Y-)(n-1)R1-R2-(R1)(n′-1)(1)，其中R1和R2独立地表示取代或未取代的芳基基团，该方法的特征在于将公式(2)的不饱和有机化合物反应：n′(R1X1n)(2)，其中n、n′和R1如上定义，而X1相同或不同且独立地表示离去基并与R1基的sp2碳原子结合，与公式(3)的硼化合物反应：mR2(BX22)n′(3)，其中R2和n′如上定义，X2表示羟基、烷氧基，存在(A)镍化合物和(B)含氮环状化合物的催化剂的存在下。
• Metalloproteinase inhibitors
  申请人：——

  公开号：US20040110809A1

  公开（公告）日：2004-06-10

  Compounds of the formula (I) useful as metalloproteinase inhibitors, especially as inhibitors of MMP12, wherein R5 is a bicyclic group. 1

  式(I)的化合物在金属蛋白酶抑制剂中有用，特别是在MMP12抑制剂中有用，其中R5是一个双环基团。
• 4-BIARYLYL-1-PHENYLAZETIDIN-2-ONES
  申请人：Martinez Eduardo J.

  公开号：US20080167255A1

  公开（公告）日：2008-07-10

  4-Biarylyl-1-phenylazetidin-2-ones useful for the treatment of hypercholesterolemia are disclosed. The compounds are of the general formula in which represents an aryl or heteroaryl residue; Ar represents an aryl residue; U is a two to six atom chain; and the R's represent substituents.

  公开了用于治疗高胆固醇血症的4-双芳基-1-苯基氮杂环戊二酮。该化合物的一般式如下：其中R表示芳基或杂芳基残基；Ar表示芳基残基；U是一个由2到6个原子组成的链；R代表取代基。