1,3-dimethyl-5-dimethylphenylsilylpyrazole | 387354-05-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,3-dimethyl-5-dimethylphenylsilylpyrazole
• 英文别名: (2,5-Dimethylpyrazol-3-yl)-dimethyl-phenylsilane
• CAS: 387354-05-4
• 化学式: C₁₃H₁₈N₂Si
• 分子量: 230.385
• InChiKey: FUBJNBNZEXMBSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-dimethylphenylsilylpyrazole 在 溴 作用下， 以 四氢呋喃 为溶剂， 生成 4,5-二溴-1,3-二甲基-1H-吡唑
  参考文献：
  名称：

  Synthesis and Reactions of Silylated and Stannylated 1,2-Azoles

  摘要：

  硅或锡4-金属化吡唑和异恶唑是通过硅烷或锡烷锡化作用从4-卤代恶唑合成的。另一方面，5-金属化吡唑是通过5-未取代吡唑与LDA反应，随后用氯硅烷和氯锡烷处理制备的。此外，从5-未取代的4-卤代吡唑出发，并应用这两种方法，得到了具有不同于三甲基硅基或三丁基锡基的不同硅基的4,5-二金属化吡唑。还研究了一些区域选择性原位取代反应。

  DOI：

  10.1055/s-2001-17699
• 作为产物：
  描述：

  1-dimethylphenylsilyl-2-trimethylsilylacetylene 在 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1,3-dimethyl-5-dimethylphenylsilylpyrazole
  参考文献：
  名称：

  Regiospecific synthesis of 5-silyl azoles

  摘要：

  5-Silylisoxazoles bearing other silyl groups different to the more usual trimethylsilyl have been prepared by condensation of silylalkynones with hydroxylamine hydrochloride. The reaction with hydrazines is more complex and leads to 5-silylpyrazoles or the corresponding hydrazones, which can be cyclized by reaction with electrophiles. This has allowed us to synthesize 5-silylpyrazoles functionalized at C-4 by groups impossible to introduce by electrophilic substitution of the pyrazole nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00386-1

文献信息

• Silylated β-enaminones as precursors in the regioselective synthesis of silyl pyrazoles
  作者：Mariola Calle、Luis A. Calvo、Alfonso González-Ortega、Ana M. González-Nogal

  DOI：10.1016/j.tet.2005.10.001

  日期：2006.1

  Silyl β-enaminones have been synthesized by reductive cleavage of 5-silyl, 3-, 4- and 5-silylmethylisoxazoles.These versatile synthons bearing different silyl groups in various positions of the enaminoketonic system are of great interest in the regioselective synthesis of 3- or 5-silylpyrazoles and 3-, 4- or 5-silylmethylpyrazoles, which can serve as building blocks in heterocyclic chemistry.

  甲硅烷基β-烯胺酮是通过还原裂解5-甲硅烷基，3-，4-和5-甲硅烷基甲基异恶唑而合成的。这些在烯胺酮体系的各个位置带有不同甲硅烷基的通用合成子对3-位区域选择性合成非常感兴趣。或5-甲硅烷基吡唑和3-，4-或5-甲硅烷基甲基吡唑，它们可以作为杂环化学的基础。
• Synthesis and Reactions of Silylated and Stannylated 1,2-Azoles
  作者：Mariola Calle、Purificación Cuadrado、Ana M. González-Nogal、Raquel Valero

  DOI：10.1055/s-2001-17699

  日期：——

  Silicon or tin 4-metalated pyrazoles and isoxazoles are synthesized by silyl- or stannylcupration from 4-haloazoles. On the other hand, 5-metalated pyrazoles are prepared by reaction of 5-unsubstituted pyrazoles with LDA and subsequent treatment with chlorosilanes and chlorostannanes. Furthermore, starting from 5-unsubstituted 4-halopyrazoles and applying both methodologies, 4,5-dimetalated pyrazoles bearing silyl groups different from trimethylsilyl or tributylstannyl groups are obtained. Some regioselective ipso-substitutions are also studied.

  硅或锡4-金属化吡唑和异恶唑是通过硅烷或锡烷锡化作用从4-卤代恶唑合成的。另一方面，5-金属化吡唑是通过5-未取代吡唑与LDA反应，随后用氯硅烷和氯锡烷处理制备的。此外，从5-未取代的4-卤代吡唑出发，并应用这两种方法，得到了具有不同于三甲基硅基或三丁基锡基的不同硅基的4,5-二金属化吡唑。还研究了一些区域选择性原位取代反应。
• Regiospecific synthesis of 5-silyl azoles
  作者：Purificación Cuadrado、Ana M González-Nogal、Raquel Valero

  DOI：10.1016/s0040-4020(02)00386-1

  日期：2002.6

  5-Silylisoxazoles bearing other silyl groups different to the more usual trimethylsilyl have been prepared by condensation of silylalkynones with hydroxylamine hydrochloride. The reaction with hydrazines is more complex and leads to 5-silylpyrazoles or the corresponding hydrazones, which can be cyclized by reaction with electrophiles. This has allowed us to synthesize 5-silylpyrazoles functionalized at C-4 by groups impossible to introduce by electrophilic substitution of the pyrazole nucleus. (C) 2002 Elsevier Science Ltd. All rights reserved.