4,4-dimethyl-2-(7-methylthieno[3,2-e][1]benzothiol-2-yl)-5H-1,3-oxazole | 187741-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4,4-dimethyl-2-(7-methylthieno[3,2-e][1]benzothiol-2-yl)-5H-1,3-oxazole
• CAS: 187741-20-4
• 化学式: C₁₆H₁₅NOS₂
• 分子量: 301.433
• InChiKey: GNULJHICKWJQHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-(7-methylthieno[3,2-e][1]benzothiol-2-yl)-5H-1,3-oxazole 在 bis-triphenylphosphine-palladium(II) chloride lithium aluminium tetrahydride 、 正丁基锂 、 碘 、 乙酸酐 、 sodium sulfate 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 1-(2-formyl-7-methylthieno[3,2-e][1]benzothiol-1-yl)-7-methylthieno[3,2-e][1]benzothiole-2-carbaldehyde
  参考文献：
  名称：

  A novel route to disubstituted [7]thiaheterohelicene via biaryl- and carbonyl-coupling reactions

  摘要：

  A new non-photochemical synthesis of disubstituted heterohelicene is described. The directed metalation at the I-position of 2-(4,4-dimethyloxazolin-2-yl)-7-methylbenzo[1,2-b:4,3-b']dithiophene was accomplished by the use of BuLi in ether to give the organolithium species which, upon treatment with iodine and chlorotributyltin, gave 2-(4,4-dimethyloxazolin-2-yl)-1-iodo-7-methylbenzo-[1,2-b:4,3-b']-dithiophene and 2-(4,4-dimethyloxazolin-2-yl)-7-methyl-1-tributylstannylbenzo-[1,2-b:4,3-b']dithiophene in high yields. Palladium-catalyzed cross-coupling between them, followed by the intramolecular McMurry coupling reaction, gave 2,13-dimethyl[7]thiaheterohelicene in good yield. Copyright (C) 1996 Elsevier Science

  DOI：

  10.1016/s0040-4039(96)02325-8
• 作为产物：
  描述：

  2-iodo-7-methylthieno[3,2-e][1]benzothiole 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 生成 4,4-dimethyl-2-(7-methylthieno[3,2-e][1]benzothiol-2-yl)-5H-1,3-oxazole
  参考文献：
  名称：

  A novel route to disubstituted [7]thiaheterohelicene via biaryl- and carbonyl-coupling reactions

  摘要：

  A new non-photochemical synthesis of disubstituted heterohelicene is described. The directed metalation at the I-position of 2-(4,4-dimethyloxazolin-2-yl)-7-methylbenzo[1,2-b:4,3-b']dithiophene was accomplished by the use of BuLi in ether to give the organolithium species which, upon treatment with iodine and chlorotributyltin, gave 2-(4,4-dimethyloxazolin-2-yl)-1-iodo-7-methylbenzo-[1,2-b:4,3-b']-dithiophene and 2-(4,4-dimethyloxazolin-2-yl)-7-methyl-1-tributylstannylbenzo-[1,2-b:4,3-b']dithiophene in high yields. Palladium-catalyzed cross-coupling between them, followed by the intramolecular McMurry coupling reaction, gave 2,13-dimethyl[7]thiaheterohelicene in good yield. Copyright (C) 1996 Elsevier Science

  DOI：

  10.1016/s0040-4039(96)02325-8