(3R,6S,9aS)-6-methyl-3-phenyl-2,3,6,7,8,9-hexahydrooxazolo[3,2-a]azepin-5(9aH)-one | 1108498-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,6S,9aS)-6-methyl-3-phenyl-2,3,6,7,8,9-hexahydrooxazolo[3,2-a]azepin-5(9aH)-one
• 英文别名: (3R,6S,9aS)-6-methyl-3-phenyl-3,6,7,8,9,9a-hexahydro-2H-[1,3]oxazolo[3,2-a]azepin-5-one
• CAS: 1108498-30-1
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: OOBCTRYKYABQKO-UBHSHLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3R,9aS)-hexahydro-3-phenyloxazolo[3,2-a]azepin-5(6H)-one 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3R,6R,9aS)-6-methyl-3-phenyl-2,3,6,7,8,9-hexahydrooxazolo[3,2-a]azepin-5(9aH)-one 、 (3R,6S,9aS)-6-methyl-3-phenyl-2,3,6,7,8,9-hexahydrooxazolo[3,2-a]azepin-5(9aH)-one
  参考文献：
  名称：

  New advances in stereoselective Meyers’ lactamization. Application to the diastereoselective synthesis of β-substituted oxazoloazepinones

  摘要：

  A stereoselective approach to the preparation of 7,5-fused bicyclic lactams based on Meyers' lactamization is presented. The lactamization step is conducted at 0 degrees C with 6-oxohexanoic acid 1 and with various chiral aminoalcohols in the presence of 2-fluoro-1-ethylpyridinium tetrafluoroborate (FEP) as an activating agent. Under these mild conditions, bicyclic lactams 2-4 were obtained in satisfactory yields and diastereoselectivities Lip to 95%. To account for the high level of diastereoselection, the mechanistic aspects of Meyers' lactamization were investigated by means of in situ infrared spectroscopy. Finally, the lactam enolate derived from 2 was subjected to reaction with various electrophiles, furnishing the corresponding beta-substituted oxazoloazepinones 5-9 in good yields (up to 86%) and in moderate to excellent diastereoselectivities ranging from 27% to 95% de. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.014

文献信息

• New advances in stereoselective Meyers’ lactamization. Application to the diastereoselective synthesis of β-substituted oxazoloazepinones
  作者：Alexis Bouet、Sylvain Oudeyer、Georges Dupas、Francis Marsais、Vincent Levacher

  DOI：10.1016/j.tetasy.2008.10.014

  日期：2008.10

  A stereoselective approach to the preparation of 7,5-fused bicyclic lactams based on Meyers' lactamization is presented. The lactamization step is conducted at 0 degrees C with 6-oxohexanoic acid 1 and with various chiral aminoalcohols in the presence of 2-fluoro-1-ethylpyridinium tetrafluoroborate (FEP) as an activating agent. Under these mild conditions, bicyclic lactams 2-4 were obtained in satisfactory yields and diastereoselectivities Lip to 95%. To account for the high level of diastereoselection, the mechanistic aspects of Meyers' lactamization were investigated by means of in situ infrared spectroscopy. Finally, the lactam enolate derived from 2 was subjected to reaction with various electrophiles, furnishing the corresponding beta-substituted oxazoloazepinones 5-9 in good yields (up to 86%) and in moderate to excellent diastereoselectivities ranging from 27% to 95% de. (C) 2008 Elsevier Ltd. All rights reserved.