3-methyl-5-tert-butyldiphenylsilylisoxazole | 460095-31-2

• 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: 3-methyl-5-tert-butyldiphenylsilylisoxazole
• 英文别名: Tert-butyl-(3-methyl-1,2-oxazol-5-yl)-diphenylsilane
• CAS: 460095-31-2
• 化学式: C₂₀H₂₃NOSi
• 分子量: 321.494
• InChiKey: ACQSDFTZAAWRTG-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±37.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-5-tert-butyldiphenylsilylisoxazole 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、2.76 MPa 条件下， 反应 24.0h， 生成 3-(tert-butyldiphenylsilyl)-1,5-dimethylpyrazole
  参考文献：
  名称：

  甲硅烷基化的β-烯胺酮作为甲硅烷基吡唑区域选择性合成的前体

  摘要：

  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。

  DOI：

  10.1016/j.tet.2005.10.001
• 作为产物：
  描述：

  4-tert-butyldiphenylsilyl-3-butyn-2-one oxime 190.0 ℃ 、13.33 Pa 条件下， 以41%的产率得到3-methyl-5-tert-butyldiphenylsilylisoxazole
  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 azolium salts and their applications in the synthesis of azolines and β-enaminoketones bearing allyl-, vinyl-, and acylsilane or α-silylketone units
  作者：Ana M. González-Nogal、Mariola Calle

  DOI：10.1016/j.tet.2009.01.114

  日期：2009.7

  Differently silylated 3- or 4-isoxazolines and 3-pyrazolines, bearing versatile vinyl- or allylsilane moieties in various positions of the heterocyclic system, have been synthesized starting from new silylazolium salts by reduction with metal complex hydrides or alkylation with organolithium reagents. On the other hand, the reductive ring-opening of silylated isoxazolium salts with lithium dimethylcuprate

  从新的甲硅烷基azo盐开始，通过金属配合物氢化物还原或用有机锂试剂烷基化，已经合成了不同的甲硅烷基化的3-或4-异恶唑啉和3-吡唑啉，在杂环系统的各个位置上带有通用的乙烯基或烯丙基硅烷部分。另一方面，甲硅烷基化的异恶唑鎓盐与二甲基二甲基碳酸锂的还原性开环产生了令人感兴趣的β-烯氨基酰基硅烷和α'-甲硅烷基甲基-β-烯氨基酮。这些多合成等同物是有机合成中有用的组成部分。
• 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。
• 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.