ethyl 2-oxo-8-(trimethylsilyl)oct-6-ynoate | 1231765-91-5

• 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: ethyl 2-oxo-8-(trimethylsilyl)oct-6-ynoate
• 英文别名: Ethyl 2-oxo-8-trimethylsilyloct-6-ynoate；ethyl 2-oxo-8-trimethylsilyloct-6-ynoate
• CAS: 1231765-91-5
• 化学式: C₁₃H₂₂O₃Si
• 分子量: 254.401
• InChiKey: PBMZERCSCAYHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-oxo-8-(trimethylsilyl)oct-6-ynoate 、 (R)-α-(氨基甲基)苄醇 以 三氟乙酸 为溶剂， 反应 0.83h， 以50%的产率得到(R)-5-phenyl-3-(6-(trimethylsilyl)hex-4-ynyl)-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids

  摘要：

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.

  DOI：

  10.1021/ol1010246
• 作为产物：
  描述：

  (6-(trimethylsilyl)hex-4-yn-1-yl)magnesium bromide 、 草酸二乙酯 以 四氢呋喃 为溶剂， 以38%的产率得到ethyl 2-oxo-8-(trimethylsilyl)oct-6-ynoate
  参考文献：
  名称：

  Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids

  摘要：

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.

  DOI：

  10.1021/ol1010246

文献信息

• Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids
  作者：Santos Fustero、Natalia Mateu、Antonio Simón-Fuentes、José Luis Aceña

  DOI：10.1021/ol1010246

  日期：2010.7.2

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.