[(E)-1,3-Diphenyl-prop-2-en-(Z)-ylidene]-phenyl-amine | 134334-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: [(E)-1,3-Diphenyl-prop-2-en-(Z)-ylidene]-phenyl-amine
• 英文别名: (2E)-N,1,3-triphenylprop-2-en-1-imine
• CAS: 134334-25-1
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: PQSZHBZUVIFFKA-QSJLUVHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [(E)-1,3-Diphenyl-prop-2-en-(Z)-ylidene]-phenyl-amine 、 水 生成 3-苯胺基-1,3-二苯基丙烷-1-酮
  参考文献：
  名称：

  EISCH J. J.; SANCHEZ RAMIRO, J. ORG. CHEM., 51,(1986) N 10, 1848-1852

  摘要：

  DOI：
• 作为产物：
  描述：

  叠氮苯 以 甲苯 为溶剂， 反应 26.0h， 生成 [(E)-1,3-Diphenyl-prop-2-en-(Z)-ylidene]-phenyl-amine
  参考文献：
  名称：

  On the reaction of (vinylimino)phosphoranes and related compounds. 20. Syntheses and properties of methanocyclodeca[b]pyridine ring systems

  摘要：

  Novel 2-[(triphenyl- and 2-[(tributylphosphoranylidene)amino]-1,6-methanol[10]annulenes (8x,y) and 3-[(triphenyl- and 3-[(tributylphosphoranylidene)amino]-1,6-methano[10]annulenes (9x,y) were generated by the Staudinger reaction of 2- and 3-azido-1,6-methano[10]annulenes (5 and 6). The compound 8x was inert to alpha,beta-unsaturated ketones, while compounds 8y and 9y were found to react with alpha,beta-unsaturated ketones in enamine-alkylation process followed by aza-Wittig reaction and dehydrogenation to give 7,12- and 5,10-methanocyclodeca[b]pyridines 20a-f and 26a,f, respectively. The reactivity of 8 and 9 as well as the site selectivity of 9 was suggested by their C-13 NMR spectra, in which the carbon signals of the nucleophilic center appear at higher field as compared to those of 1,6-methano[10]annulene. Structural properties of 20a-f and 26a,f were examined by H-1 NMR and UV spectra. The H-1 NMR spectra analyzing aromatic characters clarified both remarkable reduction of a ring current and appearance of bond alternation as compared to the parent 1,6-methano[10]annulene (1). The UV spectra exhibiting a prolonged cyclic conjugation are in contrast to their 10-pi electron analogues, 1,6-methano[10]annulene (1) and quinoline derivatives.

  DOI：

  10.1021/jo00028a040

文献信息

• Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes
  作者：Elena Yu. Schmidt、Ivan A. Bidusenko、Nadezhda I. Protsuk、Yan V. Demyanov、Igor A. Ushakov、Alexander V. Vashchenko、Boris A. Trofimov

  DOI：10.1021/acs.joc.9b03192

  日期：2020.3.6

  Aldimines react with aryl- and hetarylacetylenes in the presence of KOBut/dimethyl sulfoxide (DMSO) or NaOBut/DMSO systems under exceptionally mild conditions (14 °C, 1 h) to afford C-H-vinylated products, 1-azadienes of E configuration relative to the C-C bond, in up to 72% yield. Vinylation involves the unprecedentedly fast multiposition proton transfer in the intermediate adducts of acetylene to

  在KOBut /二甲基亚砜（DMSO）或NaOBut / DMSO系统存在下，醛亚胺在异常温和的条件下（14°C，1 h）与芳基和杂芳基乙炔反应，生成CH乙烯基化产物，相对于E构型的1-氮杂CC债券，收益率高达72％。乙烯基化涉及乙炔与C═N键的中间加合物中前所未有的快速多位质子转移。这种新的Csp2-Csp2键形成反应为合成有价值的1-氮杂二烯打开了直接的锅，原子，步和能源经济的途径。
• Dicarboxylic Acid Monoesters in β- and δ-Lactam Synthesis
  作者：Anna Ananeva、Olga Bakulina、Dmitry Dar’in、Grigory Kantin、Mikhail Krasavin

  DOI：10.3390/molecules27082469

  日期：——

  monomethyl ester of the respective dicarboxylic acid was involved in a reaction with imines promoted by acetic anhydride at an elevated temperature. Instead of the initially expected δ-lactam products of the Castagnoli-Cushman-type reaction, medicinally important 3-amino-2-azetidinones were obtained as the result of cyclization, involving a methylene group adjacent to an acid moiety. In contrast, replacing

  相应二羧酸的N-(2-甲氧基-2-氧代乙基)-N-(苯磺酰基)甘氨酸单甲酯参与了与在升高的温度下由乙酸酐促进的亚胺的反应。代替最初预期的 Castagnoli-Cushman 型反应的 δ-内酰胺产物，作为环化的结果获得了药用上重要的 3-氨基-2-氮杂环丁酮，涉及与酸部分相邻的亚甲基。相反，在同一底物中用六氟异丙基代替醇残基会使另一个亚甲基（与酯部分相邻）对以 Castagnoli-Cushman 方式提供所需的 δ-内酰胺更具反应性。