(R)-3-(hex-5-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 1231765-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: (R)-3-(hex-5-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-5-hex-5-enyl-3-phenyl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 1231765-83-5
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: PPMUJCNUOHUVJH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(hex-5-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 、 烯丙基三甲基硅烷 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R,Z)-5-phenyl-3-(7-(trimethylsilyl)hept-5-enyl)-5,6-dihydro-2H-1,4-oxazin-2-one 、 (R,E)-5-phenyl-3-(7-(trimethylsilyl)hept-5-enyl)-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：

  ethyl 2-oxooct-7-enoate 、 (R)-α-(氨基甲基)苄醇 以 三氟乙酸 为溶剂， 反应 0.83h， 以71%的产率得到(R)-3-(hex-5-enyl)-5-phenyl-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

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.