rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropionate

• 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: rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropionate
• 英文别名: methyl (2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropanoate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: LTMVADJECVHOMR-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 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

• 作为反应物：
  描述：

  rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropionate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到3-(2,3-dihydrofuran-3-yl)-2-methylpropan-1-ol
  参考文献：
  名称：

  Prostereogenic Face and Orientation Selective Oxidative Coupling Reaction between Methyl Methacrylate and 2,5-Dihydrofuran Catalyzed by a Ruthenium(0) Compound

  摘要：

  We disclose the first prostereogenic face and orientational control of coordinated olefins in an oxidative coupling reaction at a transition-metal center. Chemo-, regio-, and diastereoselective cross-dimerization between methyl methacrylate (MMA) and 2,5-dihydrofuran is catalyzed by Ru(eta(6)-naphthalene)(eta(4)-1,5-COD) (1; S mol %) at 0 degrees C in 24 h without use of solvent to give methyl rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methy1propionate (2a) in 81% yield.

  DOI：

  10.1021/om200091n
• 作为产物：
  描述：

  2,5-二氢呋喃 、 甲基丙烯酸甲酯 在 Ru(η6-naphthalene)(η4-1,5-COD) 作用下， 反应 24.0h， 以81%的产率得到rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methylpropionate
  参考文献：
  名称：

  Prostereogenic Face and Orientation Selective Oxidative Coupling Reaction between Methyl Methacrylate and 2,5-Dihydrofuran Catalyzed by a Ruthenium(0) Compound

  摘要：

  We disclose the first prostereogenic face and orientational control of coordinated olefins in an oxidative coupling reaction at a transition-metal center. Chemo-, regio-, and diastereoselective cross-dimerization between methyl methacrylate (MMA) and 2,5-dihydrofuran is catalyzed by Ru(eta(6)-naphthalene)(eta(4)-1,5-COD) (1; S mol %) at 0 degrees C in 24 h without use of solvent to give methyl rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methy1propionate (2a) in 81% yield.

  DOI：

  10.1021/om200091n

文献信息

• Asymmetric Cross-Dimerization between Methyl Methacrylate and Substituted Alkene by Ru(0)–Bicyclononadiene Complex
  作者：Yuki Hiroi、Nobuyuki Komine、Sanshiro Komiya、Masafumi Hirano

  DOI：10.1021/ol400963d

  日期：2013.5.17

  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.
• Prostereogenic Face and Orientation Selective Oxidative Coupling Reaction between Methyl Methacrylate and 2,5-Dihydrofuran Catalyzed by a Ruthenium(0) Compound
  作者：Yuki Hiroi、Nobuyuki Komine、Masafumi Hirano、Sanshiro Komiya

  DOI：10.1021/om200091n

  日期：2011.3.28

  We disclose the first prostereogenic face and orientational control of coordinated olefins in an oxidative coupling reaction at a transition-metal center. Chemo-, regio-, and diastereoselective cross-dimerization between methyl methacrylate (MMA) and 2,5-dihydrofuran is catalyzed by Ru(eta(6)-naphthalene)(eta(4)-1,5-COD) (1; S mol %) at 0 degrees C in 24 h without use of solvent to give methyl rac-(2S)-3-[(3R)-2,3-dihydrofuran-3-yl]-2-methy1propionate (2a) in 81% yield.