1-(2-formyl-7-methylthieno[3,2-e][1]benzothiol-1-yl)-7-methylthieno[3,2-e][1]benzothiole-2-carbaldehyde | 187741-26-0

• 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: 1-(2-formyl-7-methylthieno[3,2-e][1]benzothiol-1-yl)-7-methylthieno[3,2-e][1]benzothiole-2-carbaldehyde
• CAS: 187741-26-0；191532-14-6；191532-15-7
• 化学式: C₂₄H₁₄O₂S₄
• 分子量: 462.638
• InChiKey: HRXFTNYYEOCIFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-formyl-7-methylthieno[3,2-e][1]benzothiol-1-yl)-7-methylthieno[3,2-e][1]benzothiole-2-carbaldehyde 在 TiCl₃-1,2-dimethoxyethane 、 铜 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 以78%的产率得到2,13-bis(methyl)dithieno[3,2-e:3',2'-e']benzo[1,2-b:4,3-b']bis[1]benzothiophene
  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：

  7-Methylthieno[3,2-e][1]benzothiole-2-carbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 zinc(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 、 氯苯 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

文献信息

• Non-Photochemical Route to Chiral Disubstituted [7]Thiaheterohelicenes via Biaryl- and Carbonyl-Coupling Reactions
  作者：Kazuhiko Tanaka、Hitomi Suzuki、Hideji Osuga

  DOI：10.1021/jo970272t

  日期：1997.6.1

  Non-photochemical syntheses of optically active dimethyl[7]thiaheterohelicenes (P)-(+)-14 and (M)-(-)-14 are described. The key transformations in the syntheses are the metal-mediated biaryl coupling reactions between two benzodithiophene units having oxazoline moieties and the intramolecular McMurry coupling reaction of the biaryl dialdehydes (S)-13 and (R)-13. The configuration of the atropisomer 10a obtained from the biaryl coupling reaction was shown to be S by X-ray analysis.