6,7-Dimethoxy-3-thioxo-3H-benzo[c]thiophen-1-one | 315678-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,7-Dimethoxy-3-thioxo-3H-benzo[c]thiophen-1-one
• 英文别名: 6,7-Dimethoxy-3-sulfanylidene-2-benzothiophen-1-one
• CAS: 315678-13-8
• 化学式: C₁₀H₈O₃S₂
• 分子量: 240.304
• InChiKey: MKUNEZAKXYJMAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-Dimethoxy-3-thioxo-3H-benzo[c]thiophen-1-one 生成 (E)-4,5,4',5'-Tetramethoxy-[1,1']bi[benzo[c]thiophenylidene]-3,3'-dione
  参考文献：
  名称：

  First Rational Synthesis of the Thiothiono Analogue of an Unsymmetrically Substituted Phthalic Anhydride

  摘要：

  Treatment of the dithiolane derivative of an ol-carboxyethyl benzaldehyde with LDA at -78 degreesC smoothly produced the thiothionophthalic anhydride. The mechanism is proposed to involve loss of ethene and attack of an intermediate dithiocarboxylate onto the ester. Heating the thiothionophthalic an hydride gave the 3,3'-bithiophthalide.

  DOI：

  10.1021/ol0066375
• 作为产物：
  描述：

  水杨酸衍生物 在 六甲基磷酰三胺 、 正丁基锂 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6,7-Dimethoxy-3-thioxo-3H-benzo[c]thiophen-1-one
  参考文献：
  名称：

  First Rational Synthesis of the Thiothiono Analogue of an Unsymmetrically Substituted Phthalic Anhydride

  摘要：

  Treatment of the dithiolane derivative of an ol-carboxyethyl benzaldehyde with LDA at -78 degreesC smoothly produced the thiothionophthalic anhydride. The mechanism is proposed to involve loss of ethene and attack of an intermediate dithiocarboxylate onto the ester. Heating the thiothionophthalic an hydride gave the 3,3'-bithiophthalide.

  DOI：

  10.1021/ol0066375

文献信息

• Anionic cyclizations of aromatic ester dithioacetals with facially biased α,β-unsaturated ketones
  作者：Christopher F. Morrison、Craig T.M. Stamp、D. Jean Burnell

  DOI：10.1016/j.tetlet.2009.09.162

  日期：2009.12

  reacted efficiently with anions derived from aromatic ester dithioacetals to provide annulated products in a highly diastereoselective fashion. Whereas the anion of a dimethoxy aromatic ester dithiolane more rapidly reacted by an alternative intramolecular pathway, the anion of the corresponding aromatic ester dithiane was suitable for the intermolecular cyclization.

  在C-4上具有平面不对称氧官能团的环戊2-烯酮与衍生自芳族酯二硫缩醛的阴离子有效反应，以高度非对映选择性的方式提供环化产物。尽管二甲氧基芳族酯二硫杂环戊烷的阴离子通过另一种分子内途径更快速地反应，但相应的芳族酯二硫杂环戊烷的阴离子适合分子间环化。