5-Ethyl-4-((4S,5S)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-phenyl-isoxazole | 99298-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Ethyl-4-((4S,5S)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-phenyl-isoxazole
• 英文别名: 5-ethyl-4-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-3-phenyl-1,2-oxazole
• CAS: 99298-95-0
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: HTHBHLCNOCYLJX-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Ethyl-4-((4S,5S)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-phenyl-isoxazole 在 正丁基锂 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 生成 4-<4,5-dihydro-4(S)-trans-(methoxymethyl)-5(S)-phenyl-2-oxazolyl>-3-phenyl-5-((R,S)-1'-hydroxyeth-1'-yl)isoxazole
  参考文献：
  名称：

  Diastereoselectivity in the lateral metalation and electrophilic quenching of isoxazolyloxazolines

  摘要：

  Metalation and electrophilic quenching of chiral isoxazolyloxazolines at the C-5 position of the isoxazole gives rise to modest diastereoselectivity in most cases. In general, the 4(S)-(methoxymethyl)-5(S)-phenyl-2-oxazoline auxilliary (Meyer's reagent) produces the S absolute configuration at the C-5 isoxazole position of the major diastereomer, for priorities isoxazole > El > R > H. The enantiomerically pure isoxazolyloxazolines 3 can be obtained by preparative HPLC. The isoxazolyloxazolines 3 can be deprotected selectively to produce isoxazolecarboxaldehyde 4, and 4-isoxazolyl-1,4-dihydropyridine 5. The solid-state conformation of 5 is O-endo with respect to the ring juncture between the heterocyclic rings and sp, sp with respect to the 3,5-diester groups. The (+) enantiomer of IDHP 5 proved to be 2 orders of magnitude more effective in the displacement of H-3-labeled 1,4-dihydropyridine from Ca2+ channels in cardiac membranes.

  DOI：

  10.1021/jo00049a039
• 作为产物：
  描述：

  4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-phenyl-1,2-oxazole 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 5-Ethyl-4-((4S,5S)-4-methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-3-phenyl-isoxazole
  参考文献：
  名称：

  Diastereoselectivity in the lateral metalation and electrophilic quenching of isoxazolyloxazolines

  摘要：

  Metalation and electrophilic quenching of chiral isoxazolyloxazolines at the C-5 position of the isoxazole gives rise to modest diastereoselectivity in most cases. In general, the 4(S)-(methoxymethyl)-5(S)-phenyl-2-oxazoline auxilliary (Meyer's reagent) produces the S absolute configuration at the C-5 isoxazole position of the major diastereomer, for priorities isoxazole > El > R > H. The enantiomerically pure isoxazolyloxazolines 3 can be obtained by preparative HPLC. The isoxazolyloxazolines 3 can be deprotected selectively to produce isoxazolecarboxaldehyde 4, and 4-isoxazolyl-1,4-dihydropyridine 5. The solid-state conformation of 5 is O-endo with respect to the ring juncture between the heterocyclic rings and sp, sp with respect to the 3,5-diester groups. The (+) enantiomer of IDHP 5 proved to be 2 orders of magnitude more effective in the displacement of H-3-labeled 1,4-dihydropyridine from Ca2+ channels in cardiac membranes.

  DOI：

  10.1021/jo00049a039

文献信息

• Metalation of isoxazolyloxazolines, a facile route to functionally complex isoxazoles: utility, scope, and comparison to dianion methodology
  作者：Nicholas R. Natale、John I. McKenna、Chorng Shyr Niou、Mark Borth、Hakon Hope

  DOI：10.1021/jo00350a047

  日期：1985.12
• Mirzaei Yousef R., Simpson Brenda Mallet, Triggle David J., Natale Nichol+, J. Org. Chem, 57 (1992) N 23, S 6271-6279
  作者：Mirzaei Yousef R., Simpson Brenda Mallet, Triggle David J., Natale Nichol+

  DOI：——

  日期：——