2-phenyl-1-(phenylsulfonyl)-1H-benzo[d]imidazole | 15728-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-phenyl-1-(phenylsulfonyl)-1H-benzo[d]imidazole
• 英文别名: 2-phenyl-1-(phenylsulfonyl)-benzo[d]imidazole；1-benzenesulfonyl-2-phenyl-1H-benzoimidazole；1-Benzolsulfonyl-2-phenyl-benzimidazol；1-(Benzenesulfonyl)-2-phenylbenzimidazole
• CAS: 15728-50-4
• 化学式: C₁₉H₁₄N₂O₂S
• 分子量: 334.398
• InChiKey: GHIDTHQEBIJTAI-UHFFFAOYSA-N

物化性质

• 沸点：
  558.0±33.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-{[1-Phenyl-meth-(Z)-ylidene]-amino}-phenyl)-benzenesulfonamide 在 N-碘代丁二酰亚胺 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.5h， 以92%的产率得到2-phenyl-1-(phenylsulfonyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  使用N-碘代琥珀酰亚胺的分子内C（sp2）–H酰胺化

  摘要：

  据报道，在无金属条件下，使用N-碘代琥珀酰亚胺作为唯一试剂，分子内脱氢C（sp 2）H-NH偶联反应。反应在三氟乙醇作为溶剂中进行。以非常高的收率和较短的反应时间获得了几种N取代的苯并咪唑。

  DOI：

  10.1002/ejoc.201800688

文献信息

• I₂-Mediated Intramolecular C–H Amidation for the Synthesis of N-Substituted Benzimidazoles
  作者：Zhiyuan Hu、Ting Zhao、Manman Wang、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.joc.7b00142

  日期：2017.3.17

  practical intramolecular C–H amidation methodology has been developed using molecular iodine under basic conditions. The required imine substrates were readily obtained by condensation of simple o-phenylenediamine derivatives and aldehydes. The transition-metal-free cyclization reaction described here works well with crude imines and allows for the sequential synthesis of N-protected benzimidazoles

  在基本条件下，使用分子碘已开发出一种实用的分子内C–H酰胺化方法。通过简单的邻苯二胺衍生物和醛的缩合可以容易地获得所需的亚胺底物。本文所述的无过渡金属的环化反应可与粗亚胺很好地配合，无需分离较不稳定的缩合中间体，即可连续合成N-保护的苯并咪唑。这种操作简单的合成方法广泛适用于各种芳族，脂肪族和肉桂醛，以有效和可扩展的方式生产各种1,2-二取代的苯并咪唑衍生物。
• Iridium(III)-Catalyzed One-Pot Access to 1,2-Disubstituted Benzimidazoles Starting from Imidamides and Sulfonyl Azides
  作者：Linhua Xu、Lianhui Wang、Yadong Feng、Yudong Li、Lei Yang、Xiuling Cui

  DOI：10.1021/acs.orglett.7b02028

  日期：2017.8.18

  A novel Ir-catalyzed annulation of imidamides with sulfonyl azides has been developed. 1,2-Disubstituted benzimidazoles could be easily obtained in up to 99% yield for more than 40 examples. The products further streamline the synthesis of molecules that are important building blocks for organic synthesis and drug discovery. This strategy features high regioselectivity, efficieney, good tolerance of functional groups, and Mild reaction conditions.
• Kumar, P. Raja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1273 - 1274
  作者：Kumar, P. Raja

  DOI：——

  日期：——
• KUMAR, P. RAJA, INDIAN J. CHEM., 25,(1986) N 12, 1273-1274
  作者：KUMAR, P. RAJA

  DOI：——

  日期：——
• ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, AND, ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE FILM AND PATTERN FORMING METHOD, EACH USING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150004533A1

  公开（公告）日：2015-01-01

  An actinic ray-sensitive or radiation-sensitive resin composition in the present invention contains a nitrogen-containing compound (N) which is represented by the following general formula (N1): wherein, in the general formula (N1), X represents a group including a hetero atom; L represents a single bond or an alkylene group; R 2 represents a substituent, in the case where a plurality of R 2 's are present, they may be the same as or different from each other and a plurality of R 2 's may be bonded to each other to form a ring; R 3 represents a hydrogen atom or a substituent; and n represents an integer of 0 to 4.