3'-甲酰基-4-联苯甲腈 | 230647-86-6

• 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: 3'-甲酰基-4-联苯甲腈
• 英文名称: 3'-formylbiphenyl-4-carbonitrile
• 英文别名: 3'-formyl[1,1'-biphenyl]-4-carbonitrile；3-(4-cyanophenyl)benzaldehyde；4-cyano-3'-formyl-1,1'-biphenyl；3'-Formyl-[1,1'-biphenyl]-4-carbonitrile；4-(3-formylphenyl)benzonitrile
• CAS: 230647-86-6
• 化学式: C₁₄H₉NO
• 分子量: 207.232
• InChiKey: MJIMSRCIWUJRHC-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  402.5±38.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3'-甲酰基-4-联苯甲腈 在 盐酸羟胺 、 potassium tert-butylate 、 乙酸酐 、 对苯醌 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 4.0h， 生成 2-(4'-amidinobiphenyl-3-yl)-1H-benzimidazole-5-amidine tris(acetic acid) salt
  参考文献：
  名称：

  Dicationic biphenyl benzimidazole derivatives as antiprotozoal agents

  摘要：

  A series of biphenyl benzimidazoles diamidines 6a-i were synthesized from their respective diamidoximes, through the bis-O-acetoxyamidoxime followed by hydrogenation in glacial acetic acid/ethanol in the presence of Pd-C. The target compounds contain hydroxy and/or methoxy substituted 1,3-phenyl groups as the central spacer between the two amidino bearing aryl groups. All of the diamidines showed strong DNA affinities as judged by high DeltaT(m) values with poly(dA(.)dT)(2), which varied with structure and is discussed. Seven of the nine new diamidines gave in vitro IC50 values of approximately 30nM or less versus Trypanosoma brucei rhodesiense (T.b.r.). Generally the diamidines were less active versus Plasmodium falciparum (P.f), however one compound exhibited excellent activity with an IC50 value of 2.1 nM. Five of the nine diamidines exhibited excellent in vivo activity in the trypanosomal STIB900 mouse model giving 3/4 or 4/4 cures at dosage of 20mg/kg ip and three showed similar efficacy at dosage of 10mg/kg or lower. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.056
• 作为产物：
  描述：

  间溴苯甲醛 、 4-碘氰基苯 在 三甲基氯硅烷 、 1,2-二溴乙烷 、 lithium chloride 、 锌 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropiridyl)palladium(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以80%的产率得到3'-甲酰基-4-联苯甲腈
  参考文献：
  名称：

  原位生成的锌试剂与芳基氯化物，溴化物和三氟甲磺酸酯的一锅Negishi交叉偶联反应。

  摘要：

  通过将锌和LiCl添加到相应的有机碘中获得的原位生成的芳基，杂芳基，烷基或苄基多官能锌试剂，在存在下与芳基溴化物，氯化物和三氟甲磺酸酯进行平滑的Pd（0）催化的交叉偶联反应。 PEPPSI作为催化剂。该程序避免了对水和空气敏感的有机锌试剂的操作，并以高收率生产了交叉偶联产物。

  DOI：

  10.1021/jo801063c

文献信息

• [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.201001201

  日期：——

  electronically activated, non‐activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetals, lactones, amides, anilines,

  [Pd（Cl）2 P（NC 5 H 10）（C 6 H 11）2 } 2 ]（1）已通过使市售的[Pd（cod）（Cl）2 ]反应定量制备。室温下在几分钟内在N 2中与易于制备的1-（二环己基膦酰基）哌啶在甲苯中的环辛二烯）。综合大楼1已被证明是极佳的Negishi催化剂，能够将各种电子活化，非活化，失活，空间受阻，杂环和官能化的芳基溴化物与各种（也是杂环的）芳基锌试剂定量偶联，通常在几分钟内即可完成。 100°C，仅存在0.01 mol％的催化剂。含有硝基，腈，醚，酯，羟基，羰基和羧基的芳基溴化物，以及缩醛，内酯，酰胺，苯胺，烯烃，羧酸，乙酸，吡啶和嘧啶已被成功用作偶联伙伴。此外，在两个反应伙伴中都可以容忍电子和空间变化。实验观察强烈表明分子机制是有效的。
• Base-Free Suzuki–Miyaura Coupling Reaction Using Palladium(II) Supported Catalyst in Water
  作者：Ravi Tomar、Nidhi Singh、Neeraj Kumar、Vartika Tomar、Ramesh Chandra

  DOI：10.1007/s10562-019-02723-9

  日期：2019.6

  AbstractThe carbon–carbon bond formation via Suzuki–Miyaura reaction was performed in water as green solvent. Pd(OAc)2(PPh3)2 supported on magnesium hydroxide and cerium carbonate hydroxide composite was prepared and characterized by various techniques. The cross-coupling reaction of aryl halides carried out in water using mild conditions. The effects of temperature, solvents, the amount of catalyst and leaving

  摘要 通过 Suzuki-Miyaura 反应形成碳-碳键以水为绿色溶剂进行。制备了负载在氢氧化镁和碳酸铈氢氧化物上的 Pd(OAc)2(PPh3)2，并通过各种技术对其进行了表征。芳基卤化物的交叉偶联反应在温和条件下在水中进行。研究了温度、溶剂、催化剂用量和离去基团等因素对交叉偶联反应的优化条件。各种芳基卤化物以良好的产率顺利转化为联芳基化合物。此外，该催化剂在芳基卤化物的交叉偶联中也表现出稳定性和催化性能。图形摘要 开发了一种通过 Suzuki-Miyaura 反应形成碳-碳键的新方法。制备了负载在混合氢氧化镁和碳酸铈上的 2 Pd(OAc)2(PPh3)2，并通过 XRD、XPS、SEM-EDX 技术进行了表征。芳基卤化物的交叉偶联反应可以在水中和温和条件下（80°C）进行。
• [EN] ANTIBACTERIAL BIAROMATIC DERIVATIVES<br/>[FR] DÉRIVÉS BI-AROMATIQUES ANTIBACTÉRIENS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2014170821A1

  公开（公告）日：2014-10-23

  The invention relates to antibacterial compounds of formula I (I) wherein R is H, cyano, alkoxy, cyanomethoxy, cycloalkylmethoxy, hydroxyalkoxy, alkoxyalkoxy, alkoxycarbonyl, 2-ethoxy-2-oxoethoxy, 2-(methylamino)-2-oxoethoxy, (l-cyanocyclobutyl)methoxy, 3-hydroxy-pyrrolidin-l-yl or 3,4-dihydroxycyclopentyl)methoxy; U1 is N or CR1, U2 is N or CR2, U3 is N or CR3 and U4 is N or CR4, it being understood that at most three of U1, U2, U3 and U4 can be N at the same time; V1 is N or CR5, V2 is N or CR6, V3 is N or CR7 and V4 is N or CH, it being understood that at most two of V1, V2, V3 and V4 can be N at the same time; R1 is H, cyano, hydroxy or alkoxy; R2 is H, hydroxy or alkoxy; R3 is H, cyano, hydroxy, alkoxy or carboxamido; R4 is H or alkoxy; R5 is H, hydroxy or halogen; R6 is H, hydroxy or halogen; R7 is H; the dotted line "_____ " represents a bond or is absent; W represents CH or N when the dotted line "_____ " is a bond, or W represents CH2 when the dotted line "_____ " is absent; X represents CH or N; and Q represents O or S; and salts thereof.

  该发明涉及公式I（I）的抗菌化合物，其中R是H、氰基、烷氧基、氰甲氧基、环烷基甲氧基、羟基烷氧基、烷氧基烷氧基、烷氧基羰基、2-乙氧基-2-氧基乙氧基、2-(甲基氨基)-2-氧基乙氧基、(1-氰基环丁基)甲氧基、3-羟基吡咯烷-1-基或3,4-二羟基环戊基)甲氧基；U1是N或CR1，U2是N或CR2，U3是N或CR3，U4是N或CR4，理解为U1、U2、U3和U4中最多有三个可以同时为N；V1是N或CR5，V2是N或CR6，V3是N或CR7，V4是N或CH，理解为V1、V2、V3和V4中最多有两个可以同时为N；R1是H、氰基、羟基或烷氧基；R2是H、羟基或烷氧基；R3是H、氰基、羟基、烷氧基或羧胺基；R4是H或烷氧基；R5是H、羟基或卤素；R6是H、羟基或卤素；R7是H；虚线"_____"代表键或不存在；W代表CH或N，当虚线"_____"为键时，或W代表CH2，当虚线"_____"不存在时；X代表CH或N；Q代表O或S；及其盐。
• Dicationic triaryl analogs as anti-protozoan agents
  申请人：Boykin W. David

  公开号：US20050148646A1

  公开（公告）日：2005-07-07

  Novel dicationic, heterocyclic triaryl compounds are useful in the treatment of microbial infections, such as Trypanosoma brucei rhodesiense infection and Plasmodium falciparum infection. These compounds are accordingly useful in treating second-stage human African trypanosomiasis. Pharmaceutical formulations comprising these compounds can be used in methods of treating microbial infections.

  新型二元离子、杂环三芳基化合物可用于治疗微生物感染，例如Trypanosoma brucei rhodesiense感染和Plasmodium falciparum感染。因此，这些化合物可用于治疗第二阶段的人类非洲锥虫病。包含这些化合物的药物制剂可用于治疗微生物感染的方法中。
• Antibacterial Biaromatic Derivatives
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：US20160075722A1

  公开（公告）日：2016-03-17

  The invention relates to antibacterial compounds of formula I (I) wherein R is H, cyano, alkoxy, cyanomethoxy, cycloalkylmethoxy, hydroxyalkoxy, alkoxyalkoxy, alkoxycarbonyl, 2-ethoxy-2-oxoethoxy, 2-(methylamino)-2-oxoethoxy, (1-cyanocyclobutyl)methoxy, 3-hydroxy-pyrrolidin-1-yl or 3,4-dihydroxycyclopentyl)methoxy; U 1 is N or CR 1 , U 2 is N or CR 1 , U 3 is N or CR 3 and U 4 is N or CR 1 , it being understood that at most three of U 1 , U 2 , U 3 and U 4 can be N at the same time; V 1 is N or CR 5 , V 2 is N or CR 6 , V 3 is N or CR 7 and V 4 is N or CH, it being understood that at most two of V 1 , V 2 , V 3 and V4 can be N at the same time; R1 is H, cyano, hydroxy or alkoxy; R2 is H, hydroxy or alkoxy; R 3 is H, cyano, hydroxy, alkoxy or carboxamido; R 4 is H or alkoxy; R 5 is H, hydroxy or halogen; R 6 is H, hydroxy or halogen; R 7 is H; the dotted line “______” represents a bond or is absent; W represents CH or N when the dotted line “______” is a bond, or W represents CH 2 when the dotted line “______” is absent; X represents CH or N; and Q represents O or S; and salts thereof.

  本发明涉及式I的抗菌化合物（I），其中R为H，氰基，烷氧基，氰甲氧基，环烷基甲氧基，羟基烷氧基，烷氧基烷氧基，烷氧基羧酰基，2-乙氧基-2-氧代乙氧基，2-（甲基氨基）-2-氧代乙氧基，（1-氰基环丁基）甲氧基，3-羟基吡咯烷-1-基或3,4-二羟基环戊基）甲氧基；U1为N或CR1，U2为N或CR1，U3为N或CR3，U4为N或CR1，其中最多只能同时有三个U1，U2，U3和U4为N；V1为N或CR5，V2为N或CR6，V3为N或CR7，V4为N或CH，其中最多只能同时有两个V1，V2，V3和V4为N；R1为H，氰基，羟基或烷氧基；R2为H，羟基或烷氧基；R3为H，氰基，羟基，烷氧基或羧酰胺基；R4为H或烷氧基；R5为H，羟基或卤素；R6为H，羟基或卤素；R7为H；虚线“______”表示键或不存在；当虚线“______”为键时，W表示CH或N，当虚线“______”不存在时，W表示CH2；X表示CH或N；Q表示O或S；以及其盐。