2-{5-(tert-butyldimethylsilyl)oxy}pentyl-2,6-dihydro-4H-thieno[3,4-c]pyrazole 5,5-dioxide | 299178-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-{5-(tert-butyldimethylsilyl)oxy}pentyl-2,6-dihydro-4H-thieno[3,4-c]pyrazole 5,5-dioxide
• 英文别名: Tert-butyl-[5-(5,5-dioxo-4,6-dihydrothieno[3,4-c]pyrazol-2-yl)pentoxy]-dimethylsilane
• CAS: 299178-09-9
• 化学式: C₁₆H₃₀N₂O₃SSi
• 分子量: 358.577
• InChiKey: KFYXYPWIZHUVDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{5-(tert-butyldimethylsilyl)oxy}pentyl-2,6-dihydro-4H-thieno[3,4-c]pyrazole 5,5-dioxide 在 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 5-(5,5-dioxo-4H-thieno[3,4-c]pyrazol-2(6H)-yl)pentyl 2-propenoate
  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：

  4,6-二氢-1H-噻吩并[3,4-C]吡唑 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-{5-(tert-butyldimethylsilyl)oxy}pentyl-2,6-dihydro-4H-thieno[3,4-c]pyrazole 5,5-dioxide
  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

文献信息

• Type-Two Intramolecular Diels−Alder Reactions of Pyrazolo-<i>o</i>-quinodimethanes
  作者：Ta-shue Chou、Hong-Chuan Chen、Woei-Chang Yang、Wan-Sheung Li、Ito Chao、Shwu-Jiuan Lee

  DOI：10.1021/jo9917285

  日期：2000.9.1

  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.