N-Benzyl-4-methoxy-benzimidoyl chloride | 114081-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-Benzyl-4-methoxy-benzimidoyl chloride
• 英文别名: N-Benzyl-4-methoxybenzene-1-carboximidoyl chloride；N-benzyl-4-methoxybenzenecarboximidoyl chloride
• CAS: 114081-66-2
• 化学式: C₁₅H₁₄ClNO
• 分子量: 259.735
• InChiKey: ASYYLJZOTSMFLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzyl-4-methoxy-benzimidoyl chloride 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.17h， 生成 1-benzyl-2-(4-methoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

  DOI：

  10.1021/ol500864r
• 作为产物：
  描述：

  N-苄基-4-甲氧基苯甲酰胺 在 氯化亚砜 作用下， 反应 2.0h， 生成 N-Benzyl-4-methoxy-benzimidoyl chloride
  参考文献：
  名称：

  平行铜催化：多官能化氮杂环丁烷-2-亚胺的非对映选择性合成

  摘要：

  通过平行催化策略，包括铜催化的叠氮化物-炔烃环加成反应，铜催化的C sp -C sp 2交叉偶联反应和分子间反应，已经实现了高效且非对映选择性合成高度官能化的氮杂环丁烷-2-亚胺。[2 + 2]环加成。可以方便地将产物转化为结构上令人感兴趣的二氢氮杂[1,2- a ]苯并[ e ]氮杂-2-2 （4 H）-亚胺。

  DOI：

  10.1021/ol4010323

文献信息

• Semi-catalytic reduction of secondary amides to imines and aldehydes
  作者：Sun-Hwa Lee、Georgii I. Nikonov

  DOI：10.1039/c4dt00372a

  日期：——

  Ruthenium catalyzed reduction of iminoyl chlorides by HSiMe₂Ph allows for a two-step conversion of secondary amides into imines and aldehydes.

  钌催化的HSiMe2Ph还原亚胺酰氯，实现了将二级酰胺转化为亚胺和醛的两步反应。
• METHOD FOR THE CATALYTIC REDUCTION OF ACID CHLORIDES AND IMIDOYL CHLORIDES
  申请人：Nikonov Georgii

  公开号：US20140228579A1

  公开（公告）日：2014-08-14

  The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pr i 3 P)Ru(NCMe) 2 ] + [PF 6 ] − .

  本申请涉及用于催化还原酸氯化物和/或亚胺酰氯化物的方法。该方法包括在催化剂的存在下，将酸氯化物或亚胺酰氯化物与硅烷还原剂反应，所述催化剂例如为[Cp(Pr i 3 P)Ru(NCMe) 2 ] + [PF 6 ] − 。
• Nickel-catalyzed 1,4-aryl rearrangement of aryl <i>N</i>-benzylimidates <i>via</i> C–O and C–H bond cleavage
  作者：Satoshi Ogawa、Mamoru Tobisu

  DOI：10.1039/d2cc02355e

  日期：——

  We report herein that nickel-catalyzed reaction of aryl imidates bearing an N-benzyl group results in 1,4-migration of an O-aryl group via the cleavage of C–O and C–H bonds. This protocol allows for the benzylic C–H bond arylation of benzylamine building blocks using phenols as an aryl source to form elaborate diarylmethylamine derivatives.

  我们在此报道了带有N-苄基的芳基亚胺酯的镍催化反应通过C-O 和 C-H 键的断裂导致O-芳基的 1,4-迁移。该协议允许使用苯酚作为芳基来源对苄胺结构单元进行苄基 C-H 键芳基化，以形成精细的二芳基甲胺衍生物。
• New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase
  作者：Sándor Kun、Éva Bokor、Gergely Varga、Béla Szőcs、András Páhi、Katalin Czifrák、Marietta Tóth、László Juhász、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.ejmech.2014.02.041

  日期：2014.4

  O-Perbenzoylated 5-(beta-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (K-i 0.67 mu M) and the 5-(2-naphthyl)-substituted (K-i 0.41 mu M) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis of 2-Azaanthracenes via a Sequential Sonogashira Coupling/Alkynyl Imine−Allenyl Imine Isomerization/Aza-Diels−Alder/Elimination−Aromatization Reaction
  作者：Jian Cao、Xiongfa Yang、Xilin Hua、Yuan Deng、Guoqiao Lai

  DOI：10.1021/ol1028207

  日期：2011.2.4

  An Interesting sequential Sonogashira coupling/alkynyl imine-allenyl imine isomerization/aza-Diels-Aider/elimination-aromatization reaction, providing a facile synthesis of substituted 2-azaanthracenes from 1,6-dlynes and imidoyl chlorides, is reported. The easy procedure accessing the products efficiently from readily available starting materials may imply a potential synthetic application.