methyl (E)-2-methyl-3-(tetrahydrofuran-2-yl)acrylate | 1275552-72-1

• 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 (E)-2-methyl-3-(tetrahydrofuran-2-yl)acrylate
• 英文别名: methyl (E)-2-methyl-3-(oxolan-3-yl)prop-2-enoate
• CAS: 1275552-72-1
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: KLRPADDRXASYDV-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二氢呋喃 、 甲基丙烯酸甲酯 在 Ru(naphthalene)(2,6-dimethylbicyclo[3.3.1]nona-2,6-diene) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以2%的产率得到methyl (E)-2-methyl-3-(tetrahydrofuran-2-yl)acrylate
  参考文献：
  名称：

  Asymmetric Cross-Dimerization between Methyl Methacrylate and Substituted Alkene by Ru(0)–Bicyclononadiene Complex

  摘要：

  New Ru(0)-naphthalene complexes containing a bicyclononadiene ligand catalyze the linear cross-dimerization between methyl methacrylate and substituted alkenes by an oxidative coupling mechanism. The chiral (S,S)-2-methylbicyclo[3.3.1]nona-2,6-diene complex (S,5)-1b catalyzes asymmetric linear cross-dimerization between methyl methacrylate and 2,5-dihydrofuran to give the cross-dimer In 74% yield In 80% ee.

  DOI：

  10.1021/ol400963d

文献信息

• Ru(0)-catalyzed C3-selective Coupling Reactions of Unsaturated 5-Membered Heterocycles with Methyl Methacrylate and Methacryl Amide
  作者：Masafumi Hirano、Masahiro Moritake、Tasuku Murakami、Nobuyuki Komine

  DOI：10.1246/cl.170683

  日期：2017.10.5

  C3-selective direct coupling reactions of unsaturated 5-membered heterocycles such as 2,5-dihydrofuran, N-tosyl-2,5-dihydropyrrole, and 3-sulfolene with methyl methacrylate or methacryl amide are catalyzed by [Ru(η6-naphthalene)(η4-bicyclo[3.3.1]nona-2,6-diene)] (1b). As an application of this method, a pesticide lead, 2-methyl-3-(tetrahydrofuran-3-yl)propanamide (6ab) is prepared in 2 steps from 2

  [Ru(η6-naphthalene)催化不饱和5元杂环如2,5-二氢呋喃、N-甲苯磺酰基-2,5-二氢吡咯和3-环丁砜与甲基丙烯酸甲酯或甲基丙烯酰胺的C3-选择性直接偶联反应(η4-双环[3.3.1]nona-2,6-二烯)] (1b)。作为该方法的应用，从 2,5-二氢呋喃中分 2 个步骤制备了农药先导物 2-甲基-3-（四氢呋喃-3-基）丙酰胺 (6ab)，总产率为 62%。