Methyl 3-(4-methylphenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate | 855310-60-0

• 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: Methyl 3-(4-methylphenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate
• 英文别名: methyl 5-methyl-3-(4-methylphenyl)-4H-1,2-oxazole-5-carboxylate
• CAS: 855310-60-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: RIFRPJHJAYNBPY-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  311.8±52.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-(4-methylphenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Methyl-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of 4,5-dihydro-5-methylisoxazolin-5-carboxamide derivatives as VLA-4 antagonists

  摘要：

  A novel set of compounds containing a 4,5-dihydro-5-methylisoxazoline have been successfully designed as VLA-4 receptor antagonists. Compound (14p) had a high receptor binding affinity of 4 nM and also found to be metabolically stable in vitro. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.043
• 作为产物：
  描述：

  对甲基苯甲醛 在 sodium hypochlorite 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 Methyl 3-(4-methylphenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of 4,5-dihydro-5-methylisoxazolin-5-carboxamide derivatives as VLA-4 antagonists

  摘要：

  A novel set of compounds containing a 4,5-dihydro-5-methylisoxazoline have been successfully designed as VLA-4 receptor antagonists. Compound (14p) had a high receptor binding affinity of 4 nM and also found to be metabolically stable in vitro. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.043

文献信息

• Palladium-Catalyzed Synthesis of Δ²-Isoxazoline from Toluene Derivatives Enabled by the Triple Role of Silver Nitrate
  作者：Chengliang Li、Hongmei Deng、Chunju Li、Xueshun Jia、Jian Li

  DOI：10.1021/acs.orglett.5b03059

  日期：2015.11.20

  A palladium-catalyzed direct synthesis of Δ2-isoxazoline from toluene derivatives has been established. The present reaction proceeds through nondirected Csp3–H activation, benzylic nitration, dehydration, and cycloaddition. This protocol also features the unusual triple role of silver nitrate in a one-pot reaction.

  Δ的钯催化的直接合成2从甲苯衍生物-isoxazoline已经建立。本反应通过无方向的Csp 3 -H活化，苄基硝化，脱水和环加成反应进行。该方案还具有在一锅法反应中硝酸银不寻常的三重作用。
• Synthesis and evaluation of 4,5-dihydro-5-methylisoxazolin-5-carboxamide derivatives as VLA-4 antagonists
  作者：Ajay Soni、Abdul Rehman、Keshav Naik、Sunanda Dastidar、M.S. Alam、Abhijit Ray、Tridib Chaira、Vanya Shah、Venkata P. Palle、Ian A. Cliffe、Viswajanani J. Sattigeri

  DOI：10.1016/j.bmcl.2012.12.043

  日期：2013.3

  A novel set of compounds containing a 4,5-dihydro-5-methylisoxazoline have been successfully designed as VLA-4 receptor antagonists. Compound (14p) had a high receptor binding affinity of 4 nM and also found to be metabolically stable in vitro. (c) 2012 Elsevier Ltd. All rights reserved.