3-methyl-5-((R,S)-2'-hexyl)isoxazole-4-carboxylic acid | 144272-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-((R,S)-2'-hexyl)isoxazole-4-carboxylic acid
• 英文别名: 5-Hexan-2-yl-3-methyl-1,2-oxazole-4-carboxylic acid
• CAS: 144272-78-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: NGZHILSGNJZXIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-5-((R,S)-2'-hexyl)isoxazole-4-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 3-methyl-5-((R,S)-2'-hexyl)-4-<<(S)-2'-(hydroxymethyl)-N-pyrrolidino>carbonyl>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-dimethyl-2-(3-methyl-5-(2'-hexyl)isoxazolyl)oxazoline 在 盐酸 作用下， 反应 15.0h， 以87.7%的产率得到3-methyl-5-((R,S)-2'-hexyl)isoxazole-4-carboxylic acid
  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

• 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：——