N-allyl-N'-phenylbenzimidamide | 147428-52-2

• 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-allyl-N'-phenylbenzimidamide
• 英文别名: N-allyl-N'-phenylbenzamidine；N-phenyl-N'-prop-2-enylbenzenecarboximidamide
• CAS: 147428-52-2
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: SMFUPSCACITTCV-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±25.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N'-phenylbenzimidamide 在 C₃₃H₃₀N₂O₂ 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以51%的产率得到5-methyl-1,2-diphenyl-1H-imidazole
  参考文献：
  名称：

  Divergent Synthesis of Imidazoles and Quinazolines via Pd(OAc)₂-Catalyzed Annulation of N-Allylamidines

  摘要：

  A Pd(OAc)(2)-catalyzed divergent synthesis of multisubstituted imidazoles and quinazolines from N-allylamidines has been developed. In the presence of oxidant O-2 from air and/or a ligand and Pd(OAc)(2) imidazoles were obtained. Nonetheless, under microwave (MW) irradiation in a sealed system, quinazolines as major products were produced.

  DOI：

  10.1021/acs.orglett.5b01435
• 作为产物：
  描述：

  N-丙-2-烯基苯甲酰胺 在 氯化亚砜 、 三甲胺 作用下， 反应 32.0h， 生成 N-allyl-N'-phenylbenzimidamide
  参考文献：
  名称：

  Divergent Synthesis of Imidazoles and Quinazolines via Pd(OAc)₂-Catalyzed Annulation of N-Allylamidines

  摘要：

  A Pd(OAc)(2)-catalyzed divergent synthesis of multisubstituted imidazoles and quinazolines from N-allylamidines has been developed. In the presence of oxidant O-2 from air and/or a ligand and Pd(OAc)(2) imidazoles were obtained. Nonetheless, under microwave (MW) irradiation in a sealed system, quinazolines as major products were produced.

  DOI：

  10.1021/acs.orglett.5b01435

文献信息

• Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines
  作者：Jian-Ping Lin、Feng-Hua Zhang、Ya-Qiu Long

  DOI：10.1021/ol500864r

  日期：2014.6.6

  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.
• Functional group manipulation via organoselenium- and halogen-induced cyclofunctionalization/hydrolysis of allylic benzimidates, tertiary benzamides, and benzamidines. Regioflexible synthesis of amino alcohol derivatives
  作者：Lars Engman

  DOI：10.1021/jo00061a009

  日期：1993.4

  Allylic benzimidates were treated with benzeneselenenyl halides in chloroform or acetonitrile to give, via 5-exo cyclofunctionalization/hydrolysis, 3-(benzoyloxy)-2-(phenylamino)-1-(phenylselenenyl)-alkanes in fair yields. Allylic tertiary benzamides afforded 2-(benzoyloxy)-3-(phenylamino)-1-(phenylselenenyl)alkanes when submitted to similar reaction conditions. Bromoalkanes, functionalized in an analogous way, were obtained after hydrolytic workup when bromine was added to allylic benzimidates and tertiary benzamides. In some of these reactions, products of 6-endo cyclofunctionalization/hydrolysis (1-(benzoyloxy)-3-(phenylamino)-2-bromoalkanes) were also formed. The addition of benzeneselenenyl bromide to some a-substituted allylic benzimidates and tertiary benzamides was diastereoselective (0 < de < 90%, depending on conditions) with a preference for threo isomer formation. Hydrodeselenation/hydrodebromination of the cyclofunctionalization/hydrolysis products was efficiently effected (88-100% yield) by treatment of the products with triphenyltin hydride in refluxing benzene containing a catalytic amount of azobis(isobutyronitrile). The proper choice of allylic benzimidate/tertiary benzamide allowed the preparation of amino alcohol derivatives in which the 1,2-orientation of the functional groups, relative to the carbon backbone, could be varied in a controlled and predictable manner. The regioflexibility of the process was demonstrated for primary, secondary, and tertiary positions. When allylic benzamidines were submitted to the cyclofunctionalization/hydrolysis reaction conditions using benzeneselenenyl bromide as the electrophilic reagent, 5-phenylselenenyl(methyl) -substituted dihydroimidazoles were obtained.
• Divergent Synthesis of Imidazoles and Quinazolines via Pd(OAc)₂-Catalyzed Annulation of <i>N</i>-Allylamidines
  作者：Li Xu、Hongxian Li、Ziyang Liao、Kaiyan Lou、Hexin Xie、Hao Li、Wei Wang

  DOI：10.1021/acs.orglett.5b01435

  日期：2015.7.17

  A Pd(OAc)(2)-catalyzed divergent synthesis of multisubstituted imidazoles and quinazolines from N-allylamidines has been developed. In the presence of oxidant O-2 from air and/or a ligand and Pd(OAc)(2) imidazoles were obtained. Nonetheless, under microwave (MW) irradiation in a sealed system, quinazolines as major products were produced.