7-oxa-6,6-pentamethylene-2-thia-3-(thien-2-yl)bicyclo[3.3.0]octa-3-en-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-oxa-6,6-pentamethylene-2-thia-3-(thien-2-yl)bicyclo[3.3.0]octa-3-en-8-one
• 英文别名: (3aS,6aS)-2-thiophen-2-ylspiro[3a,6a-dihydrothieno[2,3-c]furan-4,1'-cyclohexane]-6-one
• 化学式: C₁₅H₁₆O₂S₂
• 分子量: 292.423
• InChiKey: YNQXXXDYJXRFMZ-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2'-联二噻吩 在 六甲基磷酰三胺 、 samarium diiodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 7-oxa-6,6-pentamethylene-2-thia-3-(thien-2-yl)bicyclo[3.3.0]octa-3-en-8-one
  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

文献信息

• Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide
  作者：Shyh-Ming Yang、Sandip Kumar Nandy、Anandakathir Robinson Selvakumar、Jim-Min Fang

  DOI：10.1021/ol006628w

  日期：2000.11.1

  [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.