三(乙胺基)硼烷 | 425392-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 三(乙胺基)硼烷
• 英文名称: 2,5-diphenylthiazole-4-carboxylic acid
• 英文别名: 2,5-diphenyl-thiazole-4-carboxylic acid；2,5-Diphenyl-thiazol-4-carbonsaeure；2,5-diphenyl-1,3-thiazole-4-carboxylic acid
• CAS: 425392-56-9
• 化学式: C₁₆H₁₁NO₂S
• 分子量: 281.335
• InChiKey: HKKJCAGVFVKYFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三(乙胺基)硼烷 在 四(三苯基膦)钯 氢氧化钾 、 potassium carbonate 、 silver nitrate 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 生成 2,4,5-三苯基-1,3-噻唑
  参考文献：
  名称：

  Regiocontrolled Synthesis of Substituted Thiazoles

  摘要：

  [GRAPHICS]The regiocontrolled synthesis of 2,5-disubstituted and 2,4,5-trisubstituted thiazoles from ethyl 2-bromo-5-chloro-4-thiazolecarboxylate 1 using sequential palladium-catalyzed coupling reactions is described.

  DOI：

  10.1021/ol025688u
• 作为产物：
  描述：

  3-溴-2-氧代-3-苯基丙酸乙酯 在 氢氧化钾 、 乙醇 作用下， 生成 三(乙胺基)硼烷
  参考文献：
  名称：

  Cook et al., Journal of the Chemical Society, 1948, p. 1056,1060

  摘要：

  DOI：

文献信息

• Fused Polycyclic Nitrogen-Containing Heterocycles: VIII. Friedel–Crafts Intramolecular Cyclization of 5-Phenylthiazole-4-carboxylic Acids—A New Route to Indeno[2,1-d]thiazoles
  作者：V. A. Mamedov、A. T. Gubaidullin、I. Z. Nurkhametova、I. A. Litvinov、Ya. A. Levin

  DOI：10.1023/b:rujo.0000036076.65278.fe

  日期：2004.4

  Friedel-Crafts intramolecular cyclization in the presence of polyphosphoric acid of 2-substituted 5-phenylthiazole-4-carboxylic acids, which are obtained by alkaline hydrolysis of the corresponding esters, leads to indeno[2,1-d]thiazoles. According to the X-ray diffraction data, packing of their molecules in crystal is determined mainly by intermolecular pi-pi contacts, regardless of the substituent nature.
• Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
  作者：Juan F. Sanz-Cervera、Raül Blasco、Julio Piera、Michael Cynamon、Ignacio Ibáñez、Marcelo Murguía、Santos Fustero

  DOI：10.1021/jo9016265

  日期：2009.12.4

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.