4-phenyl-1-phenylsulfonyl-1-azabuta-1,3-diene | 118922-13-7

• 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: 4-phenyl-1-phenylsulfonyl-1-azabuta-1,3-diene
• 英文别名: N-(3-phenylprop-2-enylidene)benzenesulfonamide；(E)-3-phenyl-1-<(phenylsulfonyl)imino>-2-propene；N-(3-phenyl-allylidene)-benzenesulfonamide；Benzenesulfonamide, N-(3-phenylallylidene)-；(NE)-N-[(E)-3-phenylprop-2-enylidene]benzenesulfonamide
• CAS: 118922-13-7
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: FLKIIIPKCJGYIM-NJKRNUQASA-N

物化性质

• 沸点：
  446.6±38.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-phenylsulfonyl-1-azabuta-1,3-diene 、 乙烯基乙醚 以 二氯甲烷 为溶剂， 25.0 ℃ 、1199.99 MPa 条件下， 反应 45.0h， 以72%的产率得到(2S^*,4R^*)-2-ethoxy-4-phenyl-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Boger, Dale L.; Corbett, Wendy L.; Curran, Timothy T., Journal of the American Chemical Society, 1991, vol. 113, # 5, p. 1713 - 1729

  摘要：

  DOI：
• 作为产物：
  描述：

  苯磺酰胺 、 肉桂醛 在 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以50%的产率得到4-phenyl-1-phenylsulfonyl-1-azabuta-1,3-diene
  参考文献：
  名称：

  Boger, Dale L.; Corbett, Wendy L.; Curran, Timothy T., Journal of the American Chemical Society, 1991, vol. 113, # 5, p. 1713 - 1729

  摘要：

  DOI：

文献信息

• Transition Metal Complexes in Organic Synthesis. Part 57: Synthesis of 1-Azabuta-1,3-dienes and Application to Catalytic Complexation of Buta-1,3-dienes and Cycloalkadienes by the Tricarbonyliron Fragment
  作者：Hans-Joachim Knölker、Birte Ahrens、Peter Gonser、Michael Heininger、Peter G. Jones

  DOI：10.1016/s0040-4020(99)01109-6

  日期：2000.4

  3-dienes 5a–g were prepared and transformed to the corresponding tricarbonyliron complexes 6. The efficiency of 6 as tricarbonyliron transfer reagents and the activity of 5a–g for the catalytic complexation with either nonacarbonyldiiron or pentacarbonyliron was investigated. It was shown that the catalytic complexation with pentacarbonyliron using the azadiene 5b as catalyst in dioxane at reflux can

  制备1-azabuta-1,3-二烯5a - g并转化为相应的三羰基铁配合物6。研究了6作为三羰基铁转移试剂的效率和5a – g与九羰基二铁或五羰基铁催化络合的活性。结果表明，将氮杂二烯5b作为催化剂在二恶烷中与五羰基铁的催化络合反应可以回流到1-甲氧基环己-1,4-二烯上。
• Inverse electron-demand aza-[4+2] cycloaddition reactions of allenamides
  作者：Craig R. Berry、Richard P. Hsung

  DOI：10.1016/j.tet.2004.05.117

  日期：2004.8

  An inverse electron-demand aza-[4+2] cycloaddition reaction of allenamides with 1-azadiene is described here. Effects of solvents on diastereoselectivity along with synthetic scopes and mechanistic insights are illustrated. Despite some synthetic limitations, this aza-[4+2] cycloaddition does provide a useful template for the synthesis of aza-glycoside related heterocycles.

  本文描述了烯丙酰胺与1-氮杂二烯的电子反需求氮杂-[4 + 2]环加成反应。说明了溶剂对非对映选择性的影响以及合成范围和机理的见解。尽管存在一些合成限制，但这种aza- [4 + 2]环加成的确为合成aza-糖苷相关的杂环提供了有用的模板。
• A general solution to implementing the 4.pi. participation of 1-aza-1,3-butadienes in Diels-Alder reactions: inverse electron demand Diels-Alder reactions of .alpha..beta.-unsaturated N-benzenesulfonyl imines
  作者：Dale L. Boger、Annette M. Kasper

  DOI：10.1021/ja00186a067

  日期：1989.2
• Croce, Piero Dalla; Ferraccioli, Raffaella; Rosa, Concetta La, Journal of the Chemical Society. Perkin transactions II, 1993, # 8, p. 1511 - 1515
  作者：Croce, Piero Dalla、Ferraccioli, Raffaella、Rosa, Concetta La、Pilati, Tullio

  DOI：——

  日期：——
• Allylic Amines via Iridium-Catalyzed C−C Bond Forming Hydrogenation:  Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents
  作者：Andriy Barchuk、Ming-Yu Ngai、Michael J. Krische

  DOI：10.1021/ja073018j

  日期：2007.7.1

  Exposure of aromatic, heteroaromatic, and aliphatic N-arylsulfonyl aldimines 1a-12a in toluene solution at 60 degrees C to 2-butyne and hydrogen at ambient pressure in the presence of a cationic iridium(I) catalyst modified by BIPHEP enables formation of reductive coupling products, allylic amines 1b-12b, in good isolated yields as single geometrical isomers (> 95:5, E:Z). The nonsymmetric alkynes 4-methyl-2-pentyne couple to imines 1b-12b under standard conditions with complete levels of regioselection. Hydrogenative coupling of 2-hexyne to imines 6a, 12a, and 13a delivers allylic amines 15b, 16b, and 18b in 10:1 regioisomeric ratios in each case. As revealed by H-2 NMR analysis, reductive coupling of 2-butyne to imine 2a under an atmosphere of elemental deuterium provides deuterio-2b, which incorporates deuterium at the vinylic position (83% H-2) and at the allylic methyl groups (5% H-2). An equal distribution of deuterium at the allylic methyl groups suggests H-D exchange at the propargylic positions of 2-butyne in advance of C-C coupling.