N-Benzyl-4-methyl-benzimidoyl chloride | 114081-67-3

• 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-Benzyl-4-methyl-benzimidoyl chloride
• 英文别名: N-benzyl-4-methylbenzenecarboximidoyl chloride
• CAS: 114081-67-3
• 化学式: C₁₅H₁₄ClN
• 分子量: 243.736
• InChiKey: ZJEGVEKTUVZUHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Benzyl-4-methyl-benzimidoyl chloride 在 potassium tert-butylate 、 氯 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 (4-Methoxy-phenyl)-(6-phenyl-4-p-tolyl-6H-[1,3,5]thiadiazin-2-yl)-amine
  参考文献：
  名称：

  Zyabrev; Chernega; Drach, Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1645 - 1651

  摘要：

  DOI：
• 作为产物：
  描述：

  苄胺 在 氯化亚砜 、 三乙胺 、 calcium chloride 作用下， 反应 4.0h， 生成 N-Benzyl-4-methyl-benzimidoyl chloride
  参考文献：
  名称：

  New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.02.041

文献信息

• Parallel Copper Catalysis: Diastereoselective Synthesis of Polyfunctionalized Azetidin-2-imines
  作者：Yanpeng Xing、Hongyang Zhao、Qiongyi Shang、Jing Wang、Ping Lu、Yanguang Wang

  DOI：10.1021/ol4010323

  日期：2013.6.7

  diastereoselective synthesis of highly functionalized azetidin-2-imines has been achieved through a parallel catalysis strategy, including a copper-catalyzed azide–alkyne cycloaddition, a copper-catalyzed Csp–Csp2 cross-coupling reaction, and an intermolecular [2 + 2] cycloaddition. The products could be conveniently converted into the structurally interesting dihydroazeto[1,2-a]benzo[e]azepin-2(4H)-imines

  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。
• Tandem synthesis of 1-(alkylamino)-2,4-diarylpyrimido[6,1-a]isoquinolin-5-ium chlorides from isoquinoline, N-alkyl-benzimidoyl chlorides, and isocyanides
  作者：Issa Yavari、Gholamhossein Khalili、Anvar Mirzaei

  DOI：10.1016/j.tetlet.2009.12.097

  日期：2010.2

  1-(Alkylamino)-2,4-diarylpyrimido[6,1-a]isoquinolin-5-ium chlorides are obtained in good yields via a tandem reaction between isoquinoline, N-alkyl-benzimidoyl chlorides and alkyl isocyanides in anhydrous acetonitrile.

  通过在无水乙腈中异喹啉，N-烷基-苯甲酰氯和烷基异氰化物之间的串联反应，可以高收率获得1-（烷基氨基）-2,4-二芳基嘧啶[6,1- a ]异喹啉-5-鎓氯化物。
• 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。
• [EN] GLYCOGEN PHOSPHORYLASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHORYLASE DE GLYCOGÈNE
  申请人：DEBRECENI EGYETEM

  公开号：WO2013061105A8

  公开（公告）日：2013-09-19
• 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.