4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-phenyl-1,2-oxazole | 93599-45-2

• 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: 4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-phenyl-1,2-oxazole
• CAS: 93599-45-2
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: QRMQEJISKZDCPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 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：
  47.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-phenyl-1,2-oxazole 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 反应 2.67h， 生成 (5-isopropyl-3-phenylisoxazol-4-yl)methanol
  参考文献：
  名称：

  Metalation of isoxazolyloxazolines, a facile route to functionally complex isoxazoles: utility, scope, and comparison to dianion methodology

  摘要：

  DOI：

  10.1021/jo00350a047
• 作为产物：
  描述：

  5-甲基-3-苯基-4-异唑甲酰氯 在 正丁基锂 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-phenyl-1,2-oxazole
  参考文献：
  名称：

  Metalation of isoxazolyloxazolines, a facile route to functionally complex isoxazoles: utility, scope, and comparison to dianion methodology

  摘要：

  DOI：

  10.1021/jo00350a047

文献信息

• A facile synthesis of functionally complex isoxazole derivatives
  作者：N.R. Natale、Chorng-Shyr Niou

  DOI：10.1016/0040-4039(84)80036-2

  日期：——

  takes place initially and selectively on the C-5′-alkyl group. Subsequent metalation also proceeds at this position. Selective deprotection of the oxazoline was accomplished without disturbing the isoxazole ring.

  2（4'-异恶唑基）的金属化-Δ 2 -oxazolines发生起初有选择地在C-5'-烷基。随后的金属化也在该位置进行。在不干扰异恶唑环的情况下完成了对恶唑啉的选择性脱保护。
• 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.
• 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：——
• NATALE, N. R.;MCKENNA, J. I.;NIOU, CHORNG-SHYR;BORTH, M.;HOPE, H., J. ORG. CHEM., 1985, 50, N 26, 5660-5666
  作者：NATALE, N. R.、MCKENNA, J. I.、NIOU, CHORNG-SHYR、BORTH, M.、HOPE, H.

  DOI：——

  日期：——
• NATALE, N. R.;NIOU, CHORNG-SHYR, TETRAHEDRON LETT., 1984, 25, N 36, 3943-3946
  作者：NATALE, N. R.、NIOU, CHORNG-SHYR

  DOI：——

  日期：——