5-(1-hydroxynonyl)-2-(2-methoxycarbonylethylidene)-5H-thiophene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(1-hydroxynonyl)-2-(2-methoxycarbonylethylidene)-5H-thiophene
• 英文别名: methyl (3Z)-3-[2-(1-hydroxynonyl)-2H-thiophen-5-ylidene]propanoate
• 化学式: C₁₇H₂₈O₃S
• 分子量: 312.474
• InChiKey: KTIOTHAKLUIKCI-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(1-hydroxynonyl)-2-(2-methoxycarbonylethylidene)-5H-thiophene 在 镍 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以79%的产率得到(+)-8-hydroxyhexadecanoic acid methyl ester
  参考文献：
  名称：

  Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide

  摘要：

  [GRAPHICS]Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl)acrylate, and methyl 5,2'-bithiophene-2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4,5-dianion, heptanoate 7-anion, and nonanoate-8,9-dianion. By the promotion of samarium diiodide, these thiophene incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings, Long-chain esters with remote hydroxyl and carboxyl groups, including an antiarthritis agent, a shellac component, and an inhibitory agent of spore germination, were prepared after reductive desulfurizatian on Raney nickel.

  DOI：

  10.1021/ol006628w
• 作为产物：
  描述：

  壬醛 、 3-(噻吩-2-基)丙烯酸甲酯 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 5-(1-hydroxynonyl)-2-(2-methoxycarbonylethylidene)-5H-thiophene
  参考文献：
  名称：

  Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide

  摘要：

  [GRAPHICS]Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl)acrylate, and methyl 5,2'-bithiophene-2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4,5-dianion, heptanoate 7-anion, and nonanoate-8,9-dianion. By the promotion of samarium diiodide, these thiophene incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings, Long-chain esters with remote hydroxyl and carboxyl groups, including an antiarthritis agent, a shellac component, and an inhibitory agent of spore germination, were prepared after reductive desulfurizatian on Raney nickel.

  DOI：

  10.1021/ol006628w