4,7-Di-naphthalen-2-yl-5,6-dihydro-benzo[b]thiophene-2-carboxylic acid ethyl ester | 418756-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,7-Di-naphthalen-2-yl-5,6-dihydro-benzo[b]thiophene-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 4,7-dinaphthalen-2-yl-5,6-dihydro-1-benzothiophene-2-carboxylate
• CAS: 418756-56-6
• 化学式: C₃₁H₂₄O₂S
• 分子量: 460.596
• InChiKey: HOURPPBBTCZWQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 4,7-Di-naphthalen-2-yl-5,6-dihydro-benzo[b]thiophene-2-carboxylic acid ethyl ester 以 甲苯 为溶剂， 反应 48.0h， 以12%的产率得到ethyl 6-aza-4,8-di(naphth-2-yl)-5,7-dioxo-6-phenyl-1-thia-tetracyclo-[7.3.2^4,8.0^3a,8a.0^4a,7a]tetradeca-2,3a(8a)-diene-2carboxylate
  参考文献：
  名称：

  A Novel Photochromic System of 4,5-Dialkenylthiophenes Constructed by the Samarium Diiodide Promoted Coupling Reactions of Thiophene-2-carboxylate with Aryl Ketones

  摘要：

  [GRAPHICS]The Sml(2)-promoted coupling reaction of ethyl thiophene-2-carboxylate with aryl ketones (2 equiv), followed by acid-catalyzed dehydration and oxidative aromatization, gave dialkenylthlophenes 1b-d, which underwent electrocyclizations upon irradiation with 300-nm light in CH3CN solution to give the corresponding closed-ring species with absorption lambda(max) approximate to 425 nm. The interconversion between dialkenylthiophenes and their corresponding closed-ring species constitutes a novel photochromic system bearing an ester group for potential uses in linkage and wavelength tuning.

  DOI：

  10.1021/ol0172830
• 作为产物：
  描述：

  4,5-bis[1-(2-naphth-2-yl)ethenyl]thiophene-2-carboxylate 以 氘代氯仿 为溶剂， 生成 ethyl 4,5-di(naphth-2-yl)benzo[b]thiophene-2-carboxylate 、 ethyl 4,5-di(naphth-2-yl)-6,7-dihydrobenzo[b]thiophene-2-carboxylate 、 4,7-Di-naphthalen-2-yl-5,6-dihydro-benzo[b]thiophene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  A Novel Photochromic System of 4,5-Dialkenylthiophenes Constructed by the Samarium Diiodide Promoted Coupling Reactions of Thiophene-2-carboxylate with Aryl Ketones

  摘要：

  [GRAPHICS]The Sml(2)-promoted coupling reaction of ethyl thiophene-2-carboxylate with aryl ketones (2 equiv), followed by acid-catalyzed dehydration and oxidative aromatization, gave dialkenylthlophenes 1b-d, which underwent electrocyclizations upon irradiation with 300-nm light in CH3CN solution to give the corresponding closed-ring species with absorption lambda(max) approximate to 425 nm. The interconversion between dialkenylthiophenes and their corresponding closed-ring species constitutes a novel photochromic system bearing an ester group for potential uses in linkage and wavelength tuning.

  DOI：

  10.1021/ol0172830