ethyl 2-[(2S,3R)-1-methoxy-3-methylpentan-2-ylamino]cyclohex-1-enecarboxylate | 1018827-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: ethyl 2-[(2S,3R)-1-methoxy-3-methylpentan-2-ylamino]cyclohex-1-enecarboxylate
• CAS: 1018827-88-7
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: PKMBIBBXTCXFCF-IUODEOHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2S,3R)-1-methoxy-3-methylpentan-2-ylamino]cyclohex-1-enecarboxylate 、 苯乙炔 在 indium(III) triflate 、 正丁基锂 、 溶剂黄146 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 8.0h， 以92%的产率得到ethyl (R)-2-oxo-1-(1-phenylvinyl)cyclohexanecarboxylate
  参考文献：
  名称：

  Construction of a Chiral Quaternary Carbon Center by Indium-Catalyzed Asymmetric α-Alkenylation of β-Ketoesters

  摘要：

  Construction of a nonracemic all-carbon quaternary stereocenter at the a-position of beta-ketoesters was achieved by way of an indium(III)-catalyzed diastereoselective alpha-alkenylation reaction of chiral enamines with 1-alkynes. The enamine bearing a chiral auxiliary derived from L-isoleucine was added to the alkyne to give an alpha-alkenylated product in excellent yield and with a stereoselectivity better than 90% ee. One can ascribe the high selectivity to a chelate intermediate involving the auxiliary and the metal atom and the high yield to efficient interactions between the indium(III) atom and the alkyne. The selectivity increased as the reaction temperature was raised to 120 degrees C and decreased at higher temperatures.

  DOI：

  10.1021/ja710408f
• 作为产物：
  描述：

  (2S,3R)-1-methoxy-3-methylpentan-2-amine 、 2-环己酮甲酸乙酯 在 4 A molecular sieve 作用下， 以 正己烷 为溶剂， 生成 ethyl 2-[(2S,3R)-1-methoxy-3-methylpentan-2-ylamino]cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Construction of a Chiral Quaternary Carbon Center by Indium-Catalyzed Asymmetric α-Alkenylation of β-Ketoesters

  摘要：

  Construction of a nonracemic all-carbon quaternary stereocenter at the a-position of beta-ketoesters was achieved by way of an indium(III)-catalyzed diastereoselective alpha-alkenylation reaction of chiral enamines with 1-alkynes. The enamine bearing a chiral auxiliary derived from L-isoleucine was added to the alkyne to give an alpha-alkenylated product in excellent yield and with a stereoselectivity better than 90% ee. One can ascribe the high selectivity to a chelate intermediate involving the auxiliary and the metal atom and the high yield to efficient interactions between the indium(III) atom and the alkyne. The selectivity increased as the reaction temperature was raised to 120 degrees C and decreased at higher temperatures.

  DOI：

  10.1021/ja710408f