4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-methyl-isoxazole | 93599-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-methyl-isoxazole
• 英文别名: 4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-ethyl-3-methyl-1,2-oxazole
• CAS: 93599-39-4
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: KAKBSANXYXHTSM-UHFFFAOYSA-N

物化性质

• 沸点：
  88 °C(Press: 0.4 Torr)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-methyl-isoxazole 在 正丁基锂 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 4-<4,5-dihydro-4(S)-trans-(methoxymethyl)-5(S)-phenyl-2-oxazolyl>-3-methyl-5-((R,S)-1'-hydroxyeth-2'-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：

  3,5-二甲基异噁唑-4-甲酰氯 在 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-methyl-isoxazole
  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。
• 4-Isoxazolyl-1,4-dihydropyridines exhibit binding at the multidrug-resistance transporter
  作者：Victoria Hulubei、Scott B. Meikrantz、David A. Quincy、Tina Houle、John I. McKenna、Mark E. Rogers、Scott Steiger、N.R. Natale

  DOI：10.1016/j.bmc.2012.09.022

  日期：2012.11

  The 4-isoxazolyl-dihydropyridines (IDHPs) exhibit inhibition of the multidrug-resistance transporter (MDR-1), and exhibit an SAR distinct from their activity at voltage gated calcium channels (VGCC). Among the four most active IDHPs, three were branched at C-5 of the isoxazole, including the most active analog, 1k. (C) 2012 Elsevier Ltd. All rights reserved.
• 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：——