(4aS,8aS)-N-benzyloxycarbonyl-2,4,4a,5,8,8a-hexahydro-1H-benzo[d][1,3]oxazinan-4-one | 1443768-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (4aS,8aS)-N-benzyloxycarbonyl-2,4,4a,5,8,8a-hexahydro-1H-benzo[d][1,3]oxazinan-4-one
• 英文别名: benzyl (4aS,8aS)-4-oxo-4a,5,8,8a-tetrahydro-2H-3,1-benzoxazine-1-carboxylate
• CAS: 1443768-78-2
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: REZOBZGSBJHPCH-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aS,8aS)-N-benzyloxycarbonyl-2,4,4a,5,8,8a-hexahydro-1H-benzo[d][1,3]oxazinan-4-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(1S,6S)-6-{[(benzyloxy)carbonyl](methyl)amino}cyclohex-3-ene-1-carboxylic acid
  参考文献：
  名称：

  Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones

  摘要：

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.016
• 作为产物：
  描述：

  (4S)-N-benzyloxycarbonyl-4-allyl-1,3-oxazinan-6-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.67h， 生成 (4aS,8aS)-N-benzyloxycarbonyl-2,4,4a,5,8,8a-hexahydro-1H-benzo[d][1,3]oxazinan-4-one
  参考文献：
  名称：

  Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones

  摘要：

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.016

文献信息

• Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones
  作者：Brad E. Sleebs、Nghi H. Nguyen、Andrew B. Hughes

  DOI：10.1016/j.tet.2013.05.016

  日期：2013.7

  The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.