N-(4-Methoxybenzylidene)-5-methyl-3-isoxazolamine | 88812-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-Methoxybenzylidene)-5-methyl-3-isoxazolamine
• 英文别名: 1-(4-methoxyphenyl)-N-(5-methyl-1,2-oxazol-3-yl)methanimine
• CAS: 88812-69-5
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: KYMRMSRSUPWBOP-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  388.8±37.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  N-(4-Methoxybenzylidene)-5-methyl-3-isoxazolamine 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 6-(4-Methoxyphenyl)-1-(5-methyl-1,2-oxazol-3-yl)-3-phenyl-4-sulfanylidene-1,3,5-triazinan-2-one
  参考文献：
  名称：

  Rajanarendar; Raju; Reddy, M. Nagi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 2, p. 223 - 228

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 4-甲氧基苯甲醛 以 甲醇 为溶剂， 反应 0.5h， 生成 N-(4-Methoxybenzylidene)-5-methyl-3-isoxazolamine
  参考文献：
  名称：

  氨基异恶唑和芳香醛反应的异常产物

  摘要：

  摘要 伯胺与醛反应通常会产生席夫碱。在这项工作中，我们介绍了在 5-甲基-3-氨基异恶唑 (3AMI) 或 3-甲基-5-反应中获得的产物的研究结果（NMR、ATR-FTIR、UV-Vis 和 X 射线）氨基异恶唑 (5AMI) 与 17 种不同的醛。基于结果，我们证明了这种简单而众所周知的反应并不总是导致获得典型的产品。此外，我们还讨论了所研究的邻羟基亚胺化合物在溶液和固态中优选的互变异构形式。了解赋予席夫碱的互变异构形式存在于溶液中和固态中，对于医学和药学以及配位化学的发展非常重要。

  DOI：

  10.1016/j.molstruc.2021.131320

文献信息

• A Fast and Highly Efficient Protocol for Reductive Amination of Aromatic Aldehydes Using NaBH4 and Isoxazole Amines in an Ionic Liquid Medium
  作者：Rajanarendar Eligeti、Siva Rami Reddy Atthunuri、Raju Samala、Firoz Pasha Shaik、Govardhan Reddy Kundur

  DOI：10.1002/cjoc.201190155

  日期：2011.4

  Reductive amination of aromatic aldehydes using NaBH4 and isoxazole amines is carried out in a Brønsted acidic ionic liquid 1‐methylimidazolium tetrafluoroborate [(HMIm)BF4]. The ionic liquid plays dual roles of solvent as well as catalyst for the efficient transformation of aromatic aldehydes to heterocyclic substituted amines in excellent yields without any undesired side product formation. The newly

  使用NaBH 4和异恶唑胺对芳香族醛进行还原胺化反应是在布朗斯台德酸性离子液体1-甲基咪唑四氟硼酸盐[（HMIm）BF 4 ]中进行的。离子液体起着溶剂和催化剂的双重作用，用于以优异的收率有效地将芳族醛转化为杂环取代的胺，而不会形成任何不希望的副产物。新合成的化合物（3，6和7通过IR）进行了表征1 H NMR和质谱技术。
• Features of 3-amino-5-methylisoxazole in heterocyclizations involving pyruvic acids
  作者：Alisa D. Morozova、Elena A. Muravyova、Svitlana V. Shishkina、Dmytro Sysoiev、Toma Glasnov、Vladimir I. Musatov、Sergey M. Desenko、Valentyn A. Chebanov

  DOI：10.1007/s10593-019-02422-8

  日期：2019.1

  The chemical properties of 3-amino-5-methylisoxazole in the reactions involving pyruvic acid derivatives are reported. The multicomponent condensation of 3-amino-5-methylisoxazole, aromatic aldehyde, and pyruvic acid was not effective while the treatment of the starting amine with pyruvic acid derivatives led to suitable synthetic procedures for selective synthesis of furanones and pyrrolones. It was

  据报道在涉及丙酮酸衍生物的反应中3-氨基-5-甲基异恶唑的化学性质。3-氨基-5-甲基异恶唑，芳族醛和丙酮酸的多组分缩合反应无效，而用丙酮酸衍生物处理起始胺导致了合适的合成方法，可选择性合成呋喃酮和吡咯烷酮。已经确定，只有3-氨基-5-甲基异恶唑的NH 2-亲核中心参与丙酮酸衍生物的杂环化。
• Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety
  作者：Hang Wang、Ju-fang Yan、Xiao-li Song、Li Fan、Jin Xu、Guang-ming Zhou、Li Jiang、Da-cheng Yang

  DOI：10.1016/j.bmc.2012.01.028

  日期：2012.3

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.
• Sallaja; Thirmal Rao; Rajanarendar, Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 200 - 201
  作者：Sallaja、Thirmal Rao、Rajanarendar、Krishnamurthy

  DOI：——

  日期：——
• Rajanarendar; Govardhan Reddy; Ramakrishna, Indian Journal of Heterocyclic Chemistry, 2012, vol. 21, # 3, p. 213 - 216
  作者：Rajanarendar、Govardhan Reddy、Ramakrishna

  DOI：——

  日期：——