(E)-2-([2,2'-bithiophen]-5-yl)-5-styryl-2H-tetrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: (E)-2-([2,2'-bithiophen]-5-yl)-5-styryl-2H-tetrazole
• 英文别名: 5-[(E)-2-phenylethenyl]-2-(5-thiophen-2-ylthiophen-2-yl)tetrazole
• 化学式: C₁₇H₁₂N₄S₂
• 分子量: 336.441
• InChiKey: NOIJUBZBDLUGHC-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-2-([2,2'-bithiophen]-5-yl)-5-styryl-2H-tetrazole 、 富马酸二甲酯 以 乙腈 为溶剂， 反应 1.0h， 以87%的产率得到(±)-(4S,5R)-dimethyl 1-([2,2'-bithiophen]-5-yl)-3-((E)-styryl)-4,5-dihydro-1H-pyrazole-4,5-dicarboxylate
  参考文献：
  名称：

  Design and Synthesis of Laser-Activatable Tetrazoles for a Fast and Fluorogenic Red-Emitting 1,3-Dipolar Cycloaddition Reaction

  摘要：

  The design and synthesis of a new class of laser light activatable tetrazoles with extended it-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s(-1). The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

  DOI：

  10.1021/ol402645q
• 作为产物：
  描述：

  肉桂腈 在 sodium azide 、 copper diacetate 、 三乙胺盐酸盐 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 44.0h， 生成 (E)-2-([2,2'-bithiophen]-5-yl)-5-styryl-2H-tetrazole
  参考文献：
  名称：

  Design and Synthesis of Laser-Activatable Tetrazoles for a Fast and Fluorogenic Red-Emitting 1,3-Dipolar Cycloaddition Reaction

  摘要：

  The design and synthesis of a new class of laser light activatable tetrazoles with extended it-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s(-1). The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

  DOI：

  10.1021/ol402645q

文献信息

• Design and Synthesis of Laser-Activatable Tetrazoles for a Fast and Fluorogenic Red-Emitting 1,3-Dipolar Cycloaddition Reaction
  作者：Peng An、Zhipeng Yu、Qing Lin

  DOI：10.1021/ol402645q

  日期：2013.11

  The design and synthesis of a new class of laser light activatable tetrazoles with extended it-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s(-1). The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.