4-(4,4-dimethyl-4,5-dihydro-2-oxazolinyl)-5-methyl-3-phenylisoxazole | 93599-37-2

• 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-4,5-dihydro-2-oxazolinyl)-5-methyl-3-phenylisoxazole
• 英文别名: 4,4-dimethyl-2-(5'-methyl-3'-phenylisoxazol-4'-yl)-Δ²-oxazoline；4-(4',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-5-methyl-3-phenylisoxazole；4-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-5-methyl-3-phenyl-1,2-oxazole
• CAS: 93599-37-2
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: DBNMLLGEKHVLIV-UHFFFAOYSA-N

物化性质

• 熔点：
  43-46 °C
• 沸点：
  415.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-4,5-dihydro-2-oxazolinyl)-5-methyl-3-phenylisoxazole 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 反应 4.67h， 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 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成 4-(4,4-dimethyl-4,5-dihydro-2-oxazolinyl)-5-methyl-3-phenylisoxazole
  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。
• Metalation and Electrophilic Quenching of C-4 Functionalized Isoxazoles; VIII. Preparation of Derivatives of 5-Thioalkylisoxazoles
  作者：T. N. Balasubramaniam、Yousef R. Mirzaei、N. R. Natale

  DOI：10.1055/s-1990-27099

  日期：——

  The lateral metalation and electrophilic quenching of isoxazoles bearing electron withdrawing groups in the 4-position 1 with disulfides, represents a selective, direct and synthetically useful entry to the thioalkyl derivatives 2 (nine examples). One exception to the formation of monothioalkyl major products was observed for the dianion of 4-[(2-hydroxymethyl-1-pyrrolidinyl)carbonyl]-3,5-dimethylisoxazole (1i) which was found to produce the 5-[bis(phenylthio)methyl]isoxazole derivative 3i as the major isolated product (66%). Oxidation of 2a with 3-chloroperoxybenzoic acid (MCPBA) proceeds selectively at sulfur in the presence of both isoxazole and oxazoline nitrogens to give the corresponding sulfoxide 4a (56%) or sulfone 5a (72%), respectively.

  在 4-位 1 上带有吸电子基团的异恶唑与二硫化物的横向金属化和亲电子猝灭代表了硫代烷基衍生物 2 的选择性、直接和合成上有用的进入（九个例子）。 对于 4-[(2-羟甲基-1-吡咯烷基)羰基]-3,5-二甲基异恶唑 (1i) 的二阴离子，观察到形成单硫代烷基主要产物的一个例外，发现它会产生 5-[双(苯硫基) )甲基]异恶唑衍生物 3i 作为主要分离产物 (66%)。在异恶唑和恶唑啉氮存在下，用 3-氯过苯甲酸 (MCPBA) 选择性地对硫进行氧化，分别得到相应的亚砜 4a (56%) 或砜 5a (72%)。
• Mosher, Michael D.; Natale, Nicholas R., Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1385 - 1388
  作者：Mosher, Michael D.、Natale, Nicholas R.

  DOI：——

  日期：——
• 4-Isoxazolyl-1,4-dihydropyridines: biological, theoretical, and structural studies
  作者：N. R. Natale、David J. Triggle、Robert B. Palmer、Barbara J. Lefler、W. Daniel Edwards

  DOI：10.1021/jm00170a032

  日期：1990.8

  Biological activity was determined for a series of seven isoxazolyldihydropyridines (IDHPs). The highest biological activity was observed for 5-alkyl-3-phenyl-IDHP (1), for which the O-endo conformation at the ring juncture between the heterocyclic rings is known in the solid state. The 3,5-dialkyl-IDHPs were intermediate in overall activity. A theoretical study of rotation about this ring juncture was performed to estimate the relative energy and barrier to rotation for the different conformers as a function of both the ring juncture between the heterocyclic rings and the esters in the 3- and 5-position of the dihydropyridine. Molecular mechanics predicts the minimum energy conformer to be O-exo-ap,ap, while quantum mechanical calculations predict O-exo-sp,sp as the minimum-energy conformer. Both methods indicate that the barrier to rotation about the heterocyclic ring juncture should be relative low, but both methods appear to overestimate the difficulty of ester rotation. A single-crystal X-ray diffractometry study of the (3,5-dimethylisoxazolyl)dihydropyridine 2 was carried out, and shows the O-endo ring juncture and sp,sp ester conformation. 2D NOESY NMR spectroscopy indicates the presence of both conformations about the ring juncture, at room temperature, as evidenced by correlations for both alkyl groups on the isoxazole with the C-2 methyl on the DHP moiety. The ap ester conformer was also evidenced by NOESY, indicating that ester interconversion must take place.
• Mirzaei, Yousef R.; Balasubramaniam, T. N.; Lefler, Barbara J., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2001 - 2004
  作者：Mirzaei, Yousef R.、Balasubramaniam, T. N.、Lefler, Barbara J.、Natale, N. R.

  DOI：——

  日期：——