N-pivaloyl-N'-n-butylbenzamidine

• 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-pivaloyl-N'-n-butylbenzamidine
• 英文别名: N-(N-butyl-C-phenylcarbonimidoyl)-2,2-dimethylpropanamide
• 化学式: C₁₆H₂₄N₂O
• 分子量: 260.379
• InChiKey: CEOVZRYBIIDTBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 N-pivaloyl-N'-n-butylbenzamidine 以 乙醚 、 二氯甲烷 为溶剂， 以89%的产率得到bis(N-pivaloyl-N'-n-butylbenzamidine)palladium(II) chloride
  参考文献：
  名称：

  [DE] N'-SUBSTITUIERTE N-ACYLAMIDIN - ÜBERGANGSMETALLKOMPLEXE UND DEREN VERWENDUNG ALS KATALYSATOREN
  [EN] N'-SUBSTITUTED N-ACYLAMIDINE METAL TRANSITION COMPLEXES AND THEIR USE AS CATALYSTS
  [FR] COMPLEXES DE METAUX DE TRANSITION N-ACYLAMIDINE N'-SUBSTITUES ET UTILISATION EN TANT QUE CATALYSEURS

  摘要：

  本发明涉及一般式（I）中M为过渡金属，选自镍、铜、钌、铑、钯、锇、铱和铂金属组，X为Cl、Br、三氟甲磺酸盐、甲磺酸盐或对甲苯磺酸盐，m为0、1或2，n为1、2或3，残基具有以下含义：R1、R2为直链或支链、环状碳氢基团，含有1至20个碳原子，可以是单烯或多烯的，含有3至6个环节的芳香基团，直接或通过C1至C6烷基或C2至C6烷基链连接，所述残基可以携带一个或多个取代基。Ar为C6至C10芳基或含氮芳基，含有5至10个环节，所述残基可经过C1至C6烷基、C1至C4卤代烷基、NR10R11、COOR6、Si(R7)3Si(R7)2R8、OR3和/或卤素取代。此外，本发明涉及一种制备这一新类过渡金属配合物的方法以及它们作为催化剂的用途。

  公开号：

  WO2004050670A1
• 作为产物：
  描述：

  N-butylbenzimidamide 、 特戊醛 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以85%的产率得到N-pivaloyl-N'-n-butylbenzamidine
  参考文献：
  名称：

  N-Acylamidine Palladium(II) Complexes. Synthesis, Structures, and Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reactions:  Experiments and DFT Calculations

  摘要：

  N-Acylamidines 2 are easily prepared by acylation of amidines 1. Upon treatment with PdCl2(PhCN)(2), they form 2:1 PdCl2 complexes 3 with trans configuration, acting as monodentate ligands via the nitrogen atom remote from the carbonyl group. The structures of the complexes 3a-c in the solid state were obtained by X-ray crystallography. As studied by DFT calculations on 2:1 model complexes, many isomeric structures 6 with different conformations and configurations are associated with local minima on the energy hyperface within an energy range of 4 kcal/mol. The complexes 3 show very high catalytic activity in Suzuki-Miyaura cross-coupling reactions, either as isolated crystals or prepared in situ without isolation.

  DOI：

  10.1021/jo034455t

文献信息

• N'-substituded n-acylamidine metal transition complexes and their use as catalysts
  申请人：Eberhardt Kurt Jan

  公开号：US20060069275A1

  公开（公告）日：2006-03-30

  The invention relates to N′-substituted N-acylamidine transition metal complexes of the general formula (I), wherein M represents a transition metal, selected from the group of metals including Ni, Cu, Ru, Rh, Pd, Os, Ir and Pt, X represents Cl, Br, triflate, methane sulfonate or p-toluol sulfonate, m is 0, 1 or 2, n is 1, 2 or 3 and the radicals have the following meanings: R 1 , R 2 is a straight-chain or branched, cyclic hydrocarbon group with 1 to 20 carbon atoms which can be mono or poly-unsaturated, an aromatic group with 3 to 6 chain members, which is linked directly or via a C 1 to C 6 alkyl or C 2 to C 6 alkylene group, whereby the mentioned groups can carry one or more substituents. Ar represents C 6 to C 10 aryl or hetaryl with 5 to 10 ring members, whereby the mentioned groups can be substituted by C 1 to C 6 alkyl, C 1 to C 4 halogenalkyl, NR 10 R 11 , COOR 6 , Si(R 7 ) 3 Si(R 7 ) 2 R 8 , OR 3 and/or halogen. The invention also relates to a method for producing this new class of metal transition complexes and their use as catalysts.

  本发明涉及一般式(I)的N'-取代N-酰胺过渡金属配合物，其中M代表从包括Ni，Cu，Ru，Rh，Pd，Os，Ir和Pt金属组中选择的过渡金属，X代表Cl，Br，三氟甲烷磺酸盐，甲烷磺酸盐或对甲苯磺酸盐，m为0，1或2，n为1，2或3，基团具有以下含义：R1，R2是直链或支链，具有1至20个碳原子的环烷烃基，可以是单或多不饱和的，是具有3到6个链成员的芳香基团，直接或通过C1到C6烷基或C2到C6亚烷基基团连接，所述基团可以携带一个或多个取代基。Ar代表具有5到10个环成员的C6到C10芳基或杂芳基，所述基团可以通过C1到C6烷基，C1到C4卤代烷基，NR10R11，COOR6，Si(R7)3Si(R7)2R8，OR3和/或卤素进行取代。本发明还涉及制备这种新型过渡金属配合物的方法以及它们作为催化剂的用途。
• N -SUBSTITUIERTE N-ACYLAMIDIN - BERGANGSMETALLKOMPLEXE UND DEREN VERWENDUNG ALS KATALYSATOREN
  申请人：BASF Aktiengesellschaft

  公开号：EP1569947A1

  公开（公告）日：2005-09-07
• N -SUBSTITUIERTE N-ACYLAMIDIN - ÜBERGANGSMETALLKOMPLEXE UND DEREN VERWENDUNG ALS KATALYSATOREN
  申请人：BASF Aktiengesellschaft

  公开号：EP1569947B1

  公开（公告）日：2006-08-30
• US7141687B2
  申请人：——

  公开号：US7141687B2

  公开（公告）日：2006-11-28
• <i>N-</i>Acylamidine Palladium(II) Complexes. Synthesis, Structures, and Catalytic Activity for Suzuki−Miyaura Cross-Coupling Reactions:  Experiments and DFT Calculations
  作者：Jan K. Eberhardt、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/jo034455t

  日期：2003.8.1

  N-Acylamidines 2 are easily prepared by acylation of amidines 1. Upon treatment with PdCl2(PhCN)(2), they form 2:1 PdCl2 complexes 3 with trans configuration, acting as monodentate ligands via the nitrogen atom remote from the carbonyl group. The structures of the complexes 3a-c in the solid state were obtained by X-ray crystallography. As studied by DFT calculations on 2:1 model complexes, many isomeric structures 6 with different conformations and configurations are associated with local minima on the energy hyperface within an energy range of 4 kcal/mol. The complexes 3 show very high catalytic activity in Suzuki-Miyaura cross-coupling reactions, either as isolated crystals or prepared in situ without isolation.