4-methyl-5-phenyl-2-(trifluoromethyl)oxazole | 141118-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-methyl-5-phenyl-2-(trifluoromethyl)oxazole
• 英文别名: 4-Methyl-5-phenyl-2-(trifluoromethyl)-1,3-oxazole
• CAS: 141118-78-7
• 化学式: C₁₁H₈F₃NO
• 分子量: 227.186
• InChiKey: QIPWXPNILDXXNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Trifluoro-acetic acid (Z)-2-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-1-phenyl-propenyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 4-methyl-5-phenyl-2-(trifluoromethyl)oxazole
  参考文献：
  名称：

  Synthesis of oxazoles from O-trimethylsilyl acyltrimethylsilane cyanohydrins

  摘要：

  Sequential addition of organolithium reagents and acyl chlorides (or anhydrides) to O-trimethylsilyl acyltrimethylsilane cyanohydrins affords beta-(acyloxy)-N,N-bis(trimethylsilyl) enamines which cyclize to substituted oxazoles under thermolysis or treatment with trimethylsilyl trifluoromethanesulfonate. Oxazoles were prepared containing alkyl and phenyl substituents at C-5, alkyl, alkenyl, and phenyl substituents at C-4, and alkyl, alkenyl, phenyl, and functionalized substituents at C-2.

  DOI：

  10.1021/jo00038a020

文献信息

• A bench-stable <i>N</i>-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles
  作者：Yusuke Kobayashi、Sota Masakado、Takuya Murai、Shohei Hamada、Takumi Furuta、Yoshiji Takemoto

  DOI：10.1039/d1ob00947h

  日期：——

  ortho-Nitro-substituted N-trifluoroacetyl imino-λ3-iodane is a bench-stable trifluoroacetyl nitrene precursor, in which intra- and intermolecular halogen bonding (XB) plays an important role. Potential synthetic applications of this novel precursor were explored.

  邻-硝基取代的N-三氟乙酰亚氨基-λ 3 -碘烷是一种稳定的三氟乙酰氮烯前体，其中分子内和分子间卤素键（XB）起着重要作用。探索了这种新型前体的潜在合成应用。
• Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles
  作者：Vladimir Motornov、Petr Beier

  DOI：10.1021/acs.orglett.2c00359

  日期：2022.3.18

  pentafluoropropionic anhydrides) by nitrogen acylation and acid-mediated triazole ring opening. Structurally diverse fluoroalkylated oxazoles were prepared from 4,5-disubstituted-1,2,3-triazoles. Efficient synthesis of 2-acylaminoketones was achieved from 4-substituted 1,2,3-triazoles. Finally, easy access to fluoroalkylated imidazoles and 1,2,4-triazines was developed by a one-pot two-step route from

  NH-1,2,3-三唑在与氟化酸酐（三氟乙酸、二氟乙酸、氯二氟乙酸和五氟丙酸酐）的反应中通过氮酰化和酸介导的三唑开环进行开环。结构多样的氟烷基化恶唑由 4,5-二取代-1,2,3-三唑制备。从 4-取代的 1,2,3-三唑实现了 2-酰基氨基酮的高效合成。最后，通过从 NH-三唑、氟化酸酐和胺或肼的一锅两步路线开发了易于获得氟烷基化咪唑和 1,2,4-三嗪的方法。