5-bromo-2-(2-bromomethyl-2-propenyl)-4-chlorobenzonitrile | 671795-65-6

• 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: 5-bromo-2-(2-bromomethyl-2-propenyl)-4-chlorobenzonitrile
• 英文别名: 5-Bromo-2-[2-(bromomethyl)prop-2-en-1-yl]-4-chlorobenzonitrile；5-bromo-2-[2-(bromomethyl)prop-2-enyl]-4-chlorobenzonitrile
• CAS: 671795-65-6
• 化学式: C₁₁H₈Br₂ClN
• 分子量: 349.452
• InChiKey: GTCQUKJOWAXSSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(2-bromomethyl-2-propenyl)-4-chlorobenzonitrile 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 9-bromo-8-chloro-5,6-dihydro-4H-1,2,3,3a-tetraazabenzo[e]azulen-5-one
  参考文献：
  名称：

  Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines

  摘要：

  A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.

  DOI：

  10.1021/jo035498c
• 作为产物：
  描述：

  2-氨基-4-氯苯腈 在 N-溴代丁二酰亚胺(NBS) 、 亚硝酸特丁酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 5-bromo-2-(2-bromomethyl-2-propenyl)-4-chlorobenzonitrile
  参考文献：
  名称：

  Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines

  摘要：

  A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.

  DOI：

  10.1021/jo035498c

文献信息

• Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and <i>N</i>-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines
  作者：Fredrik Ek、Sophie Manner、Lars-Göran Wistrand、Torbjörn Frejd

  DOI：10.1021/jo035498c

  日期：2004.2.1

  A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N-3 followed by an intramolecular N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.