2,4-diphenyl-5-[(trimethylsilyl)methyl]oxazole | 1140505-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-diphenyl-5-[(trimethylsilyl)methyl]oxazole
• 英文别名: (2,4-Diphenyl-1,3-oxazol-5-yl)methyl-trimethylsilane
• CAS: 1140505-05-0
• 化学式: C₁₉H₂₁NOSi
• 分子量: 307.467
• InChiKey: MKXJEMNWALSIIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-phenyl-3-(trimethylsilyl)prop-2-ynyl)benzamide 在 gold(III) bromide 、 水 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以76%的产率得到2,4-diphenyl-5-[(trimethylsilyl)methyl]oxazole
  参考文献：
  名称：

  金催化取代环异构化 3-三甲基甲硅烷基炔丙基醇和酰胺高效一锅法合成取代恶唑

  摘要：

  3-Trimethylsilylpropargylic alcohols 1, on treatment with amides 2 in the presence of catalytic amounts of cationic gold(III), underwent propargylic substitution followed by cycloisomerization, in which the key feature is the beta-cation-stabilizing effect of the silicon atom of 1.

  DOI：

  10.3987/com-18-s(t)81

文献信息

• Brønsted Acid-Catalyzed Propargylation/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Substituted Oxazoles from Propargylic Alcohols and Amides
  作者：Ying-ming Pan、Fei-jian Zheng、Hai-xin Lin、Zhuang-ping Zhan

  DOI：10.1021/jo8027533

  日期：2009.4.17

  An efficient one-pot propargylation/cycloisomerization tandem process has been developed for the synthesis of substituted oxazole derivatives from propargylic alcohols and amides with use of p-toluenesulfonic acid monohydrate (PTSA) as a bifunctional catalyst. This method provides a rapid and efficient access to substituted oxazoles.

  已经开发了一种有效的一锅炔丙基化/环异构化串联方法，该方法使用对甲苯磺酸一水合物（PTSA）作为双功能催化剂，由炔丙醇和酰胺合成取代的恶唑衍生物。此方法可快速有效地获得取代的恶唑。
• Iron Trichloride Catalyzed One-Pot Synthesis of Substituted Oxazoles from Propargylic Acetates and Amides under Microwave Irradiation
  作者：Wen-Wen Xu、Min Lin、Yang Huang、Li Chen、Zhuang-Ping Zhan

  DOI：10.2174/157017809790442970

  日期：2009.12.1

  A rapid and efficient procedure under microwave irradiation, using silica gel-supported reagents for the synthesis of substitued oxazoles has been developed through iron trichloride catalyzed propargylation/cycloisomerization tandem reaction of propargylic acetates and amides.

  通过三氯化铁催化丙炔基乙酸酯和酰胺的丙炔基化/环异构化串联反应，开发了一种在微波辐照下使用硅胶支撑试剂合成取代恶唑的快速高效程序。
• Efficient One-Pot Synthesis of Substituted Oxazoles from 3-Trimethylsilylpropargylic Alcohols and Amides by Gold-Catalyzed Substitution Followed by Cycloisomerization
  作者：Osamu Tamura、Nobuyoshi Morita、Aoi Sano、Shino Aonuma、Arisa Matsunaga、Yoshimitsu Hashimoto

  DOI：10.3987/com-18-s(t)81

  日期：——

  3-Trimethylsilylpropargylic alcohols 1, on treatment with amides 2 in the presence of catalytic amounts of cationic gold(III), underwent propargylic substitution followed by cycloisomerization, in which the key feature is the beta-cation-stabilizing effect of the silicon atom of 1.