1-{3-(tert-butyldimethylsilyl)oxy}propyl-4,6-dihydro-1H-thieno[3,4-c]pyrazole | 299177-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{3-(tert-butyldimethylsilyl)oxy}propyl-4,6-dihydro-1H-thieno[3,4-c]pyrazole
• 英文别名: Tert-butyl-[3-(4,6-dihydrothieno[3,4-c]pyrazol-1-yl)propoxy]-dimethylsilane
• CAS: 299177-92-7
• 化学式: C₁₄H₂₆N₂OSSi
• 分子量: 298.525
• InChiKey: ZDJKVVJROUTOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{3-(tert-butyldimethylsilyl)oxy}propyl-4,6-dihydro-1H-thieno[3,4-c]pyrazole 在 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 3-(5,5-Dioxo-5,6-dihydro-4H-5λ⁶-thieno[3,4-c]pyrazol-1-yl)-propan-1-ol
  参考文献：
  名称：

  Type-Two Intramolecular Diels−Alder Reactions of Pyrazolo-o-quinodimethanes

  摘要：

  Two isomeric series of homologous N-(acryloyloxy)alkylated pyrazolo-3-sulfolenes 10a-c and 18a-c have been efficiently synthesized from a common starting material, 4,6-dihydro-1H-thieno[3,4-c]-pyrazole (5). Thermolysis of these fused 3-sulfolenes provides the corresponding o-quinodimethanes which simultaneously undergo "type-two" intramolecular Diels-Alder reactions to form two- and three-atom-bridged tricyclic pyrazoles which are otherwise difficult to prepare. It was also demostrated that, depending on the N-substitution position of the pyrazolo-fused 3-sulfolenes, the temperature required for the thermal extrusion of SO2 and the regioselectivity of the T2-IMDA reactions were influenced substantially.

  DOI：

  10.1021/jo9917285
• 作为产物：
  描述：

  1-碘-3-[(叔-丁基二甲基硅烷基)氧基]丙烷 、 4,6-二氢-1H-噻吩并[3,4-C]吡唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到2-{3-(tert-butyldimethylsilyl)oxy}propyl-2,6-dihydro-4H-thieno[3,4-c]pyrazole
  参考文献：
  名称：

  Type-Two Intramolecular Diels−Alder Reactions of Pyrazolo-o-quinodimethanes

  摘要：

  Two isomeric series of homologous N-(acryloyloxy)alkylated pyrazolo-3-sulfolenes 10a-c and 18a-c have been efficiently synthesized from a common starting material, 4,6-dihydro-1H-thieno[3,4-c]-pyrazole (5). Thermolysis of these fused 3-sulfolenes provides the corresponding o-quinodimethanes which simultaneously undergo "type-two" intramolecular Diels-Alder reactions to form two- and three-atom-bridged tricyclic pyrazoles which are otherwise difficult to prepare. It was also demostrated that, depending on the N-substitution position of the pyrazolo-fused 3-sulfolenes, the temperature required for the thermal extrusion of SO2 and the regioselectivity of the T2-IMDA reactions were influenced substantially.

  DOI：

  10.1021/jo9917285