4H-thieno<3,4-c>benzopyran | 151254-12-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4H-thieno<3,4-c>benzopyran
• 英文别名: ethyl 3-phenyl-9b-hydroxy-1,3,3,3a,9b-tetrahydro-4H-thieno<3,4-c>benzopyrane-1-carboxylate；9b-hydroxy-3-phenyl-1,3,3a,9b-tetrahydro-4H-thieno<3,4-c>benzopyrane-1-carboxylate d'ethyle
• CAS: 151254-12-5
• 化学式: C₂₀H₂₀O₄S
• 分子量: 356.442
• InChiKey: AOCZLRAOVKXACW-WOGUSJMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (E)-3-benzylidenechroman-4-one 、 巯基乙酸乙酯 在 哌啶 作用下， 以 氘代苯 为溶剂， 生成 4H-thieno<3,4-c>benzopyran
  参考文献：
  名称：

  Robert, JF.; Alhassan, M.; Xicluna, A., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 788 - 797

  摘要：

  DOI：

文献信息

• Etude RMN1H et radiocristallographique de la stéreochimie de 3-aryl-9b-hydroxy-1,3,3a,9b-tétrahydro-4H-thiéno[3,4-c] benzo[e]pyrane-1-carboxylates d'éthyle. Configuration et conformation
  作者：M. Alhassan、J.F. Robert、A. Xicluna、J.E. Ombetta、R. Mercier、B. Laude

  DOI：10.1016/0584-8539(93)80070-q

  日期：1993.7

  The reaction of ethyl mercaptoacetate with some 3-aryliden-4-chromanones yields the corresponding ethyl 3-aryl-9b-hydroxy-1,3,3a,9b-tetrahydro-4H-thieno[3,4-c]benzo[e]pyrane-1-carboxylates. In spite of the presence of four chirality centers, the reaction is diastereospecific and gives a single diastereoisomer whose configuration and conformation were specified by its PMR data.The cis-fused tetrahydrothiophenic and dihydropyranic cycles lie in half-chair conformation. The 9b-hydroxyl and tbe 3-aryl groups are in a cis equatorial and pseudoequatorial disposition. The ester group, also cis with the hydroxyl group, presents a hydrogen bond with the hydroxyl. In the presence of an ortho-substituent at the phenyl group (particularly a chlorine atom), this phenyl group undergoes a notable rotation as is pointed out by a radiocristallographic study. A comparative study between the NMR and radiocristallographic data allows the confirmation of the maintenance of the same conformation in solid and dissolved states.
• Un nouveau thiénobenzopyrane à propriétés vasodilatatrices cérébrales: le 9b-hydroxy-3-phényl-1,3,3a,9b-tétrahydro-4H-thiéno[3,4-c]benzo[e] pyrane-1-carboxylate d'éthyle
  作者：JE Ombetta、M Alhassan、JF Robert、JJ Panouse

  DOI：10.1016/0223-5234(90)90189-a

  日期：1990.9