(R)-methyl-3-cyano-4,4-dimethylpentanoate | 881315-68-0

• 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: (R)-methyl-3-cyano-4,4-dimethylpentanoate
• 英文别名: methyl (3R)-3-cyano-4,4-dimethylpentanoate
• CAS: 881315-68-0
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: XSJBUNUQJFOSBV-ZETCQYMHSA-N

物化性质

• 沸点：
  251.8±23.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl-3-cyano-4,4-dimethylpentanoate 在 镍 氢气 作用下， 以 甲醇 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 16.0h， 以90%的产率得到(R)-4-tert-butylpyrrolidin-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen

  摘要：

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.

  DOI：

  10.3987/com-05-s(k)41
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 magnesium monoperoxyphthalate hexahydrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 正己烷 为溶剂， 反应 1.0h， 生成 (R)-methyl-3-cyano-4,4-dimethylpentanoate
  参考文献：
  名称：

  Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen

  摘要：

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.

  DOI：

  10.3987/com-05-s(k)41