4,5-dihydro-1,2-diphenyl-5-<(phenylselenenyl)methyl>-1H-imidazole | 147428-54-4

• 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: 4,5-dihydro-1,2-diphenyl-5-<(phenylselenenyl)methyl>-1H-imidazole
• 英文别名: 1,2-Diphenyl-5-(phenylselanylmethyl)-4,5-dihydroimidazole
• CAS: 147428-54-4
• 化学式: C₂₂H₂₀N₂Se
• 分子量: 391.374
• InChiKey: BQFROWKVYVQTON-UHFFFAOYSA-N

物化性质

• 沸点：
  510.4±46.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-1,2-diphenyl-5-<(phenylselenenyl)methyl>-1H-imidazole 在 偶氮二异丁腈 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以94%的产率得到(+/-)-5-methyl-1,2-diphenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jo00061a009
• 作为产物：
  描述：

  N-苯基亚胺苄基氯 在 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 27.0h， 生成 4,5-dihydro-1,2-diphenyl-5-<(phenylselenenyl)methyl>-1H-imidazole
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jo00061a009

文献信息

• 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.