methyl 6-hydroxyundecanoate | 315706-48-0

• 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: methyl 6-hydroxyundecanoate
• CAS: 315706-48-0
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: UDYXYYWYUXPOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxyundecanoate 在 lithium hydroxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 7-pentyloxepan-2-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
• 作为产物：
  描述：

  噻吩-2-羧酸甲酯 在 镍 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 methyl 6-hydroxyundecanoate
  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.