methyl 6-hydroxy-6-(4'-methylphenyl)hexanoate | 315706-45-7

• 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-hydroxy-6-(4'-methylphenyl)hexanoate
• 英文别名: Methyl 6-hydroxy-6-(4-methylphenyl)hexanoate；methyl 6-hydroxy-6-(4-methylphenyl)hexanoate
• CAS: 315706-45-7
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: CYJLXZKWLLEGML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-hydroxy-6-(4'-methylphenyl)hexanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6-Hydroxy-6-p-tolyl-hexanoic acid
  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-hydroxy-6-(4'-methylphenyl)hexanoate
  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

• Zinc Metal-Promoted Cross-Coupling Reaction of Non-Activated Alkyl Halides with Aldehydes in the Presence of Chlorotrimethylsilane
  作者：Yoshio Ishino、Takatoshi Ito、Takumi Mizuno、Akira Ishikawa、Jun-ichi Kobayashi

  DOI：10.1055/s-2002-35583

  日期：——

  Treatment of non-activated alkyl halides 1 with aldehydes 3 in the presence of zinc metal and chlorotrimethylsilane (TMSCI), DMA and/or NMP in THF brought about highly facile and effective cross-coupling to give the corresponding alcohols in good yield. These reactions are assumed to proceed through zinc reagent intermediates generated in situ.

  在金属锌和三甲基氯硅烷 (TMSCI)、DMA 和/或 NMP 的存在下，在 THF 中用醛 3 处理未活化的烷基卤化物 1 导致非常容易和有效的交叉偶联，以良好的收率得到相应的醇。假定这些反应通过原位生成的锌试剂中间体进行。