[(E)-But-2-en-(E)-ylidene]-(4-methoxy-benzyl)-amine | 183311-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(E)-But-2-en-(E)-ylidene]-(4-methoxy-benzyl)-amine
• CAS: 183311-39-9
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: XHNGCYWTNMFBBE-GUNLQBCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [(E)-But-2-en-(E)-ylidene]-(4-methoxy-benzyl)-amine 在 六甲基磷酰三胺 、 N,N-二乙基苯胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ((E)-Buta-1,3-dienyl)-[(Z)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-vinyl]-(4-methoxy-benzyl)-amine
  参考文献：
  名称：

  Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

  摘要：

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h
• 作为产物：
  描述：

  巴豆醛 、 4-甲氧基苄胺 、 苄胺 在 4 A molecular sieve 作用下， 以 乙醚 为溶剂， 生成 [(E)-But-2-en-(E)-ylidene]-(4-methoxy-benzyl)-amine
  参考文献：
  名称：

  Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

  摘要：

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h

文献信息

• Double nucleophilic addition to α,β-unsaturated aldimines induced by titanium tetrahalides
  作者：Makoto Shimizu、Asato Morita、Tomoyuki Kaga

  DOI：10.1016/s0040-4039(99)01794-3

  日期：1999.11

  2-addition with α,β-unsaturated imine to give doubly alkylated products in good yields. Moreover, a 1:1 mixture of ketene silyl acetal and allyltributylstannane reacted with α,β-unsaturated imine, where the ketene silyl acetal specifically underwent 1,4-addition reaction to give an enamine derivative, which in turn isomerized into an imine. Allyltributylstannane then reacted with the resulting imine to give

  在0.5当量的存在下。在TiX 4中，乙烯酮甲硅烷基乙缩醛先进行1,4-加成，然后再与α，β-不饱和亚胺加成1,2-，以高收率得到双烷基化产物。此外，乙烯酮甲硅烷基乙缩醛和烯丙基三丁基锡烷的1：1混合物与α，β-不饱和亚胺反应，其中所述乙烯酮甲硅烷基乙缩醛特别地进行1,4-加成反应以得到烯胺衍生物，其继而异构化成亚胺。然后使烯丙基三丁基锡烷与所得的亚胺反应，以高收率得到双烷基化产物。
• CYCLIC N-CARBOXAMIDE COMPOUNDS USEFUL AS HERBICIDES
  申请人：E. I. DU PONT DE NEMOURS AND COMPANY

  公开号：US20180213788A1

  公开（公告）日：2018-08-02

  Disclosed are compounds of Formula (1), including all stereoisomers, N-oxides, and salts thereof, (Formula (1)) wherein G, J, Q 1 , R 4 , Y 2 , Q 2 , R 5 and Y 1 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.