3-methyl-5-(1'-phenylprop-2'-yl)isoxazole-4-carbinol | 144272-74-2

• 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: 3-methyl-5-(1'-phenylprop-2'-yl)isoxazole-4-carbinol
• 英文别名: [3-Methyl-5-(1-phenylpropan-2-yl)-1,2-oxazol-4-yl]methanol
• CAS: 144272-74-2
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: BQZXTKVHVSNSDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-5-(1'-phenylprop-2'-yl)isoxazole-4-carbinol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氧气 、 copper(l) chloride 作用下， 生成 (+/-)-3-methyl-5-(1'-phenylprop-2'-yl)isoxazole-4-carbaldehyde
  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',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-3,5-dimethylisoxazole 在 盐酸 、 lithium aluminium tetrahydride 作用下， 生成 3-methyl-5-(1'-phenylprop-2'-yl)isoxazole-4-carbinol
  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：——
• Diastereoselectivity in the lateral metalation and electrophilic quenching of isoxazolyloxazolines
  作者：Yousef R. Mirzaei、Brenda Mallet Simpson、David J. Triggle、Nicholas R. Natale

  DOI：10.1021/jo00049a039

  日期：1992.11

  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.