5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole | 18354-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole
• 英文别名: 5-Tosyl-5,6-dihydro-4H-thieno<3,4-c>pyrrol；5-(toluene-4-sulfonyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole；5,6-dihydro-5-tosyl-4H-thieno[3,4-c]pyrrole；5-[(4-methylphenyl)sulfony]-5,6-dihydro-4H-thieno[3,4-c]pyrrole；5-(4-methylphenyl)sulfonyl-4,6-dihydrothieno[3,4-c]pyrrole
• CAS: 18354-71-7
• 化学式: C₁₃H₁₃NO₂S₂
• 分子量: 279.384
• InChiKey: PKMFAEROGWOLBE-UHFFFAOYSA-N

物化性质

• 沸点：
  440.6±55.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole 在 氢溴酸 、 苯酚 作用下， 以 丙酸 为溶剂， 反应 8.0h， 生成 5,6-dihydro-4H-thieno[3,4-c]pyrrole
  参考文献：
  名称：

  WO2007/87231

  摘要：

  公开号：
• 作为产物：
  描述：

  1,3-Dichlor-5-tosyl-5,6-dihydro-4H-thieno<3,4-c>pyrrol 在 钯 ammonium formate 作用下， 以 甲醇 、 水 为溶剂， 以73%的产率得到5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole
  参考文献：
  名称：

  4H-thieno[3,4-c]pyrrole derivatives

  摘要：

  Pyrrole衍生物的化学式：##STR1##其中R.sub.1代表氢原子或卤素原子，线性或支链的C.sub.1-6烷基基团，C.sub.3-6烯基基团，C.sub.1-4烷氧甲基基团，苄基，苯基（可选地被一个或多个卤素原子或烷基基团取代），一个CO.sub.2 R基团，其中R代表线性或支链的C.sub.1-4烷基基团，苯基或苄基，或一个CONR'R"基团，其中R'和R"各自独立地代表氢原子或线性或支链的C.sub.1-4烷基基团，R.sub.2代表氢原子或卤素原子或线性或支链的C.sub.1-4烷基基团，R.sub.3代表4,5-二氢-1H-咪唑-2-基或1H-咪唑-4-基团，以及它们与药学上可接受的酸形成的加合盐在治疗中作为α2-拮抗剂和α1-激动剂是有用的。

  公开号：

  US05380742A1

文献信息

• Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors
  作者：Kazuma Matsui、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1002/anie.201609545

  日期：2016.12.5

  The use of N‐(p‐chlorophenyl)methylbenzoxazole‐2‐thione as a sulfur‐atom donor enables the catalytic [2+2+1] cycloaddition of diynes in wet DMF at 80 °C when open to air, thus affording diverse fused thiophenes with good yields and wide functional‐group compatibility. A plausible mechanism, involving a cationic ruthenacycle intermediate, was also proposed on the basis of several control experiments

  使用N-（对氯苯基）甲基苯并恶唑-2-硫酮作为硫原子供体时，在空气中于80°C暴露于空气中时，可使二炔在[DMC]催化[2 + 2 + 1]环加成反应，从而提供多种熔融态噻吩具有良好的收率和广泛的官能团相容性。在一些对照实验的基础上，还提出了一种可行的机理，其中涉及阳离子钌循环中间体。
• Silver-Mediated [2 + 2 + 1] Cyclization Reaction of Diynes with Elemental Selenium/Sulfur To Synthesize 3,4-Substituted Cyclopenta[<i>c</i>]selenophenes/Cyclopenta[<i>c</i>]thiophenes
  作者：Ye Wang、Yang Yuan、Zongkang Wang、Yingge Gu、Siyi Fu、Lingkai Kong、Yanzhong Li

  DOI：10.1021/acs.orglett.1c02018

  日期：2021.8.6

  An efficient and atom-economical silver-mediated [2 + 2 + 1] cyclization protocol for the synthesis of 3,4-fused-ring-substituted and 2,5-unsubstituted selenophenes or thiophenes has been developed. Two C–Se/C–S bonds and one C–C bond were rapidly constructed in one step. Readily accessible substrates, commercially available elemental selenium/sulfur, and good functional group tolerance make this procedure

  已开发出一种高效且原子经济的银介导 [2 + 2 + 1] 环化方案，用于合成 3,4-稠环取代和 2,5-未取代的硒酚或噻吩。一步快速构建了两个 C-Se/C-S 键和一个 C-C 键。容易获得的底物、市售的元素硒/硫和良好的官能团耐受性使该过程对合成 π 共轭材料分子具有吸引力。
• 4H-thieno[3,4-c]pyrrole derivatives
  申请人：Synthelabo

  公开号：US05380742A1

  公开（公告）日：1995-01-10

  Pyrrole derivatives of formula: ##STR1## in which R.sub.1 represents a hydrogen or halogen atom, a linear or branched C.sub.1-6 alkyl group, a C.sub.3-6 alkenyl group, a C.sub.1-4 alkoxymethyl group, benzyl, a phenyl group optionally substituted by one or more halogen atoms or alkyl radicals, a CO.sub.2 R group in which R represents a linear or branched C.sub.1-4 alkyl radical, phenyl or benzyl, or a CONR'R" group in which R' and R" each represent, independently of one another, a hydrogen atom or a linear or branched C.sub.1-4 alkyl radical, R.sub.2 represents a hydrogen or halogen atom or a linear or branched C.sub.1-4 alkyl group, and R.sub.3 represents a 4,5-dihydro-1H-imidazol-2-yl or 1H-imidazol-4-yl group, and their addition salts with pharmaceutically acceptable acids are useful in therapeutics as .alpha..sub.2 -antagonists, and .alpha..sub.1 -agonists.

  Pyrrole衍生物的化学式：##STR1##其中R.sub.1代表氢原子或卤素原子，线性或支链的C.sub.1-6烷基基团，C.sub.3-6烯基基团，C.sub.1-4烷氧甲基基团，苄基，苯基（可选地被一个或多个卤素原子或烷基基团取代），一个CO.sub.2 R基团，其中R代表线性或支链的C.sub.1-4烷基基团，苯基或苄基，或一个CONR'R"基团，其中R'和R"各自独立地代表氢原子或线性或支链的C.sub.1-4烷基基团，R.sub.2代表氢原子或卤素原子或线性或支链的C.sub.1-4烷基基团，R.sub.3代表4,5-二氢-1H-咪唑-2-基或1H-咪唑-4-基团，以及它们与药学上可接受的酸形成的加合盐在治疗中作为α2-拮抗剂和α1-激动剂是有用的。
• Aminocyclohexanes as Dipeptidyl Peptidase-IV Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Biftu Tesfaye

  公开号：US20090270467A1

  公开（公告）日：2009-10-29

  The present invention is directed to novel substituted aminocyclohexanes of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式（I）的新型取代氨基环己烷，其是二肽基肽酶-IV酶的抑制剂，并且对于涉及二肽基肽酶-IV酶的疾病的治疗或预防，例如糖尿病，特别是2型糖尿病，具有用途。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及二肽基肽酶-IV酶的疾病中的使用。
• Aminocyclohexanes as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
  申请人：Merck Sharp & Dohme Corp.

  公开号：US07750034B2

  公开（公告）日：2010-07-06

  The present invention is directed to novel substituted aminocyclohexanes of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种结构式为（I）的新型取代氨基环己烷，其为二肽基肽酶-IV酶的抑制剂，可用于治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗二肽基肽酶-IV酶参与的疾病中的用途。