N,N-diethyl-4'-methoxybiphenyl-4-carboxamide | 331816-27-4

• 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: N,N-diethyl-4'-methoxybiphenyl-4-carboxamide
• 英文别名: N,N-diethyl-4′-methoxybiphenyl-4-carboxamide；N,N-diethyl-4-(4-methoxyphenyl)benzamide
• CAS: 331816-27-4
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: OCUYYHCNRFPGFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-4'-methoxybiphenyl-4-carboxamide 在 palladium on activated charcoal 、 Adam’s catalyst sodium hydroxide 、 氯化亚砜 、 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三溴化硼 、 四氯化钛 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 159.67h， 生成 4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one
  参考文献：
  名称：

  Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

  摘要：

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00980-2
• 作为产物：
  描述：

  4-甲氧基苯基溴化镁 在 C₃₈H₃₄Br₂N₄Ni₂P₂ 、 lithium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 生成 N,N-diethyl-4'-methoxybiphenyl-4-carboxamide
  参考文献：
  名称：

  Mono- and Dinuclear Pincer Nickel Catalyzed Activation and Transformation of C–Cl, C–N, and C–O Bonds

  摘要：

  Condensation of 2-NH2C6H4P(Et)Ph (2) with pyrrole-2-carboxaldehyde generated 2-(C4H4N-2'-CH-N)C6H4P(Et)Ph (3). Treatment of 3 with NaH and followed by (DME)NiX2 (X = Cl, Br) afforded mononuclear pincer nickel complexes [Ni{2-(C4H3N-2'-CH-N)C6H4P(Et)Ph}X] (4a, X = Cl; 4b, X = Br). Reaction of [2-NH2C6H4P(Ph)](2)(CH2)(n) (5a, n = 3; 5b, n = 4) with pyrrole-2-carboxaldehyde or 5-tert-butyl-1H-pyrrole-2-carbaldehyde formed [2-(C4H4N-2'-CH-N)C6H4P(Ph)](2)(CH2)(n) (6a, n = 3; 6b, n = 4) and [2-(5'-tBuC(4)H(3)N-2'-CH-N)C6H4P(Ph)](2)(CH2)(4) (6c). Respective treatment of 6ac with NaH followed by (DME)NiX2 (X = Cl, Br) gave the dinuclear nickel complexes [Ni{2-(5'-RC4H2N-2'-CH-N)C6H4P(Ph)}X](2)(CH2)(n) (7a, R = H, X = Cl, n = 3; 7b, R = H, X = Cl, n = 4; 7c, R = H, X = Br, n = 4; 7d, R = tBu, X = Cl, n = 4). Catalysis of the complexes for the activation and transformation of CCl, CN, and CO bonds was evaluated. Complex 7c exhibited excellent catalytic activity in the cross-coupling of aryl chlorides or aryltrimethylammonium iodides with arylzinc reagents as well as of aryl sulfamates with aryl Grignard reagents. The dinuclear nickel complexes 7bd showed higher catalytic activity than the mononuclear complexes in each type of reaction.

  DOI：

  10.1021/om500452c

文献信息

• P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides
  作者：Dan Wu、Zhong-Xia Wang

  DOI：10.1039/c4ob01041h

  日期：——

  were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good

  P，N，N-镍镍配合物[Ni（Cl）N（2-R 2 PC 6 H 4）（2'-Me 2 NC 6 H 4）}]（R = Ph，3a ; R = Pr i，合成了3b； R ＝ Cy，3c），并评估了它们对芳基氟化物和氯化物的Kumada或Negishi交叉偶联反应的催化作用。在室温下，配合物3a有效催化（杂）芳基氟化物与芳基格氏试剂的交叉偶联。复杂3a 它还在低催化剂负载和良好的官能团相容性下，于80°C催化（杂）芳基氯和芳基锌试剂的交叉偶联。
• Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents
  作者：Feng Zhu、Zhong-Xia Wang

  DOI：10.1021/jo500619f

  日期：2014.5.16

  Ni(PCy3)2Cl2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor and -rich aryl fluorides can react effectively with nucleophiles including aryl-, methyl-, and benzylzinc chlorides. A wide range of substituents and functional groups are tolerated. In the presence of a directing group, PhC(O), the reaction is selective for cleavage of

  Ni（PCy 3）2 Cl 2被证明可以有效地催化芳基氟化物和有机锌试剂的交叉偶联。贫电子的和富电子的芳基氟化物都可以与亲核试剂（包括芳基氯化锌，甲基氯化锌和苄基氯化锌）有效反应。宽范围的取代基和官能团是可以容忍的。在有一个直接基团PhC（O）的存在下，该反应对于在二氟芳烃中的羰基取代基裂解C-F键具有选择性。
• Cobalt-Catalyzed Cross-Coupling Reactions of Aryl Triflates and Lithium Arylborates
  作者：Hung A. Duong、Zong-Han Yeow、Yong-Lun Tiong、Nur Haidah Binte Mohamad Kamal、Wenqin Wu

  DOI：10.1021/acs.joc.9b02105

  日期：2019.10.4

  A catalyst system comprising CoCl2/IAd·HBF4 enables the Suzuki-Miyaura cross-coupling reaction of a broad range of aryl triflates and arylboronic esters that are activated by n-butyllithium.

  包含CoCl2 / IAd·HBF4的催化剂体系使Suzuki-Miyaura交联反应可实现多种被正丁基锂活化的芳基三氟甲磺酸酯和芳基硼酸酯。
• Amido Pincer Nickel Catalyzed Kumada Cross-Coupling of Aryl, Heteroaryl, and Vinyl Chlorides
  作者：Zhong-Xia Wang、Xue-Qi Zhang

  DOI：10.1055/s-0033-1339653

  日期：——

  Amido pincer nickel complexes Ni(Cl)[2-P(Ph-2)C6H4NC(Ph)=NAr]} (Ar = 4-MeC6H4, 1; Ar = 4-ClC6H4, 2; Ar = 4-MeOC6H4, 3) were shown to efficiently catalyze the cross-coupling of activated, unactivated, and deactivated aryl chlorides, N-heteroaryl chlorides, 1,4-dichlorobenzene, and vinyl chlorides with aryl Grignard reagents.
• Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel Complexes
  作者：Wang-Jun Guo、Zhong-Xia Wang

  DOI：10.1021/jo302425x

  日期：2013.2.1

  N-Heterocyclic carbene-based pincer nickel complexes were synthesized and characterized. These complexes efficiently catalyze cross-coupling of aryl Grignard reagents with aryl chlorides or fluorides under mild conditions.