4,6-二氢-1H-噻吩并[3,4-C]吡唑 | 145286-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,6-二氢-1H-噻吩并[3,4-C]吡唑
• 英文名称: 4,6-Dihydrothieno<3,4-c>pyrazole
• 英文别名: 4,6-dihydro-1H-thieno[3,4-c]pyrazole
• CAS: 145286-40-4
• 化学式: C₅H₆N₂S
• 分子量: 126.182
• InChiKey: WFUOVUVQGMHJCW-UHFFFAOYSA-N

物化性质

• 沸点：
  355.6±42.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-二氢-1H-噻吩并[3,4-C]吡唑 在 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 5-(4,6-dihydro-5,5-dioxo-1H-thieno[3,4-c]pyrazol-1-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-[(dimethylamino)methylene]dihydrothiophen-3(2H)-one 在 sodium carbonate 、 肼 作用下， 反应 2.5h， 以80%的产率得到4,6-二氢-1H-噻吩并[3,4-C]吡唑
  参考文献：
  名称：

  Access to new sulfolene derivatives via formylation of thiolan-3-one

  摘要：

  New tetrahydrothiophene derivatives, which are demonstrated to be reactive towards various nucleophiles and provide access to [b]- and [c]-fused sulfolenes are described. Application of heterocyclic sulfides as o-quinodimethane precursors is documented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.107

文献信息

• A novel “type-two” intramolecular Diels-Alder reaction leading to three-atom-bridged tricyclic pyrazoles
  作者：Ta-shue Chou、Hong-Chuan Chen

  DOI：10.1016/s0040-4039(98)02528-3

  日期：1999.1

  (Acryloyloxy)butylated pyrazolo-3-sulfolenes are thermolyzed to the corresponding o-quinodimethanes which undergo simultaneous “type-two” intramolecular Diels-Alder reactions to form two- and three-atom-bridged tricyclic pyrazoles.

  将（丙烯酰氧基）丁基化的吡唑并-3-磺基酮热解为相应的邻喹啉二甲烷，它们同时进行“二型”分子内Diels-Alder反应，形成两原子和三原子桥连的三环吡唑。
• A novel route to the preparation of pyrazole analogs of o-xylylene.
  作者：Ta Shue Chou、Ruei Chih Chang

  DOI：10.1021/jo00054a037

  日期：1993.1
• Synthesis and Reactions of N-Substituted Pyrazolo-3-sulfolenes
  作者：Ta-shue Chou、Ruei-Chih Chang

  DOI：10.3987/com-93-6535

  日期：——

  N-Toluenesulfonyl- and N-(anilinocarbonyl)pyrazolo-3-sulfolenes have been prepared from the protected oxotetrahydrothiophenecarbaldehyde (7) via a sequence of hydrazone formation, ketal hydrolysis, cyclization, dehydration, and oxidation reactions. These N-substituents migrate between the two nitrogen atoms of the pyrazole ring at different stages. Extrusion of SO2 from N-anilinocarbonylpyrazolo-3-sulfolenes was achieved at 180-200 degrees C and the transient intermediate, the pyrazolo-o-quniodimethane, could be trapped with dienophiles.