5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilylthiazole | 1175534-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilylthiazole
• 英文别名: 2-(triisopropylsilyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole；2-(Triisopropylsilyl)thiazole-5-boronic acid pinacol ester；tri(propan-2-yl)-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazol-2-yl]silane
• CAS: 1175534-91-4
• 化学式: C₁₈H₃₄BNO₂SSi
• 分子量: 367.436
• InChiKey: ZNEZXNSVTBKUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-二溴-2,2'-联噻吩 、 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilylthiazole 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium phosphate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到5,5'-bis[2-(triisopropylsilyl)thiazol-5-yl]-2,2'-bithiophene
  参考文献：
  名称：

  Electronic Tuning of Thiazolyl-Capped π-Conjugated Compounds via a Coordination/Cyclization Protocol with B(C₆F₅)₃

  摘要：

  Electronic tuning of thiazolyl-capped pi-conjugated systems via a coordination/cyclization protocol with B(C6F5)(3) effectively enhances an electron-accepting character giving rise to lower reduction potentials and increases thermal stability.

  DOI：

  10.1021/ol102282x
• 作为产物：
  描述：

  三异丙基氯硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilylthiazole
  参考文献：
  名称：

  Electronic Tuning of Thiazolyl-Capped π-Conjugated Compounds via a Coordination/Cyclization Protocol with B(C₆F₅)₃

  摘要：

  Electronic tuning of thiazolyl-capped pi-conjugated systems via a coordination/cyclization protocol with B(C6F5)(3) effectively enhances an electron-accepting character giving rise to lower reduction potentials and increases thermal stability.

  DOI：

  10.1021/ol102282x

文献信息

• Synthesis of 5-arylthiazoles. Comparative study between Suzuki cross-coupling reaction and direct arylation
  作者：Nicolas Primas、Alexandre Bouillon、Jean-Charles Lancelot、Hussein El-Kashef、Sylvain Rault

  DOI：10.1016/j.tet.2009.05.013

  日期：2009.7

  A facile synthetic route to the new thiazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-arylthiazoles. A comparative study between Suzuki cross-coupling reactions and palladium-catalyzed C5–H direct arylation on thiazole ring was achieved.

  本文描述了新的噻唑-5-基硼酸频哪醇酯的简便合成路线。研究了其对铃木交叉偶联反应的反应性以提供各种5-芳基噻唑。进行了铃木交叉偶联反应和钯催化的噻唑环上C5–H直接芳基化反应的比较研究。
• Electronic Tuning of Thiazolyl-Capped π-Conjugated Compounds via a Coordination/Cyclization Protocol with B(C₆F₅)₃
  作者：Andre Job、Atsushi Wakamiya、Gerald Kehr、Gerhard Erker、Shigehiro Yamaguchi

  DOI：10.1021/ol102282x

  日期：2010.12.3

  Electronic tuning of thiazolyl-capped pi-conjugated systems via a coordination/cyclization protocol with B(C6F5)(3) effectively enhances an electron-accepting character giving rise to lower reduction potentials and increases thermal stability.