N-[3-(4-methylphenyl)-1,2-oxazol-5-yl]acetamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[3-(4-methylphenyl)-1,2-oxazol-5-yl]acetamide
• 英文别名: N-(3-p-tolyl-isoxazol-5-yl)-acetamide；N-(3-p-Tolyl-isoxazol-5-yl)-acetamid
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD24388805
• 分子量: 216.239
• InChiKey: IHDDBNLJVYKEDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-(4-methylphenyl)-1,2-oxazol-5-yl]acetamide 在 氯磺酸 、 氯化亚砜 作用下， 反应 25.0h， 以77%的产率得到5-amino-3-[3-(chlorosulfonyl)-4-methylphenyl]-1,2-oxazole-4-sulfonyl chloride
  参考文献：
  名称：

  Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

  摘要：

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.018
• 作为产物：
  描述：

  对甲苯酰乙腈 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-[3-(4-methylphenyl)-1,2-oxazol-5-yl]acetamide
  参考文献：
  名称：

  通过 5-氨基异恶唑与偶氮萘的芳基化有机催化原子选择性构建五原子杂联二胺

  摘要：

  偶氮萘与 5-氨基异恶唑的有效催化不对称迈克尔型反应已被开发出来。该反应基于使用手性磷酸作为催化剂，以良好的产率和优异的对映选择性产生大量轴向手性杂联芳二胺。手性产物的克级反应和后修饰证明了其在手性催化剂和配体合成中的潜力。这种方法不仅为构建五原子杂联芳基支架提供了一种有用的方法，而且还为轴向手性二胺家族提供了新成员，在合成和药物化学方面具有广阔的应用前景。

  DOI：

  10.1021/acs.orglett.4c00440

文献信息

• A copper-catalyzed asymmetric Friedel–Crafts hydroxyalkylation of pyrazole-4,5-diones with 5-aminoisoxazoles
  作者：Siyu Gao、Xiang Sun、Sijie Peng、Zhenggen Zha、Qi Sun、Zhiyong Wang

  DOI：10.1039/d4ob00322e

  日期：——

  An asymmetric Friedel–Crafts hydroxyalkylation reaction of 5-aminoisoxazoles with pyrazole-4,5-diones was developed under the catalysis of 5% chiral copper complexes. This reaction exhibits functional group tolerance and excellent enantioselectivity. Moreover, the reaction can be scaled up and its mechanism was studied.

  在 5% 手性铜配合物的催化下，开发了 5-氨基异恶唑与吡唑-4,5-二酮的不对称弗里德尔-克来福特羟烷基化反应。该反应表现出官能团耐受性和优异的对映选择性。此外，该反应可以放大并研究其机理。
• Seidel, Journal fur praktische Chemie (Leipzig 1954), 1898, vol. <2> 58, p. 144
  作者：Seidel

  DOI：——

  日期：——
• Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds
  作者：Mikhail Krasavin、Mikhail Korsakov、Zhanna Zvonaryova、Evgenii Semyonychev、Tiziano Tuccinardi、Stanislav Kalinin、Muhammet Tanç、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.02.018

  日期：2017.3

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.
• Organocatalytic Atroposelective Construction of Pentatomic Heterobiaryl Diamines through Arylation of 5-Aminoisoxazoles with Azonaphthalenes
  作者：Weiwei Luo、Huanhuan Guo、Xueying Qiu、Meijun Ming、Lin Zhang、Hao Zhu、Jun Zhou

  DOI：10.1021/acs.orglett.4c00440

  日期：2024.4.5

  efficient catalytic asymmetric Michael-type reaction of azonaphthalenes with 5-aminoisoxazoles has been developed. The reaction was based on the utilization of a chiral phosphoric acid as the catalyst, delivering a large panel of axially chiral heterobiaryl diamines in generally good yields with excellent enantioselectivities. The gram-scale reaction and postmodification of the chiral product demonstrated

  偶氮萘与 5-氨基异恶唑的有效催化不对称迈克尔型反应已被开发出来。该反应基于使用手性磷酸作为催化剂，以良好的产率和优异的对映选择性产生大量轴向手性杂联芳二胺。手性产物的克级反应和后修饰证明了其在手性催化剂和配体合成中的潜力。这种方法不仅为构建五原子杂联芳基支架提供了一种有用的方法，而且还为轴向手性二胺家族提供了新成员，在合成和药物化学方面具有广阔的应用前景。