(+)-3-(benzo[b]thiophen-2-yl)-3,4,4a,5-tetrahydrocyclopenta[c]pyran-6(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (+)-3-(benzo[b]thiophen-2-yl)-3,4,4a,5-tetrahydrocyclopenta[c]pyran-6(1H)-one
• 英文别名: 3-(1-benzothiophen-2-yl)-3,4,4a,5-tetrahydro-1H-cyclopenta[c]pyran-6-one
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: BIUOVYWIKPEPOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dicobalt octacarbonyl 、 (-)-2-(1-(prop-2-ynyloxy)but-3-enyl)benzo[b]thiophene 在 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以66%的产率得到(+)-3-(benzo[b]thiophen-2-yl)-3,4,4a,5-tetrahydrocyclopenta[c]pyran-6(1H)-one
  参考文献：
  名称：

  Design, stereoselective synthesis and computational calculations of novel hybrid compounds via Pauson-Khand reactions

  摘要：

  A series of novel chiral hybrid compounds between benzofuran and bicyclic cyclopentenone and also benzothiophene and bicyclic cyclopentenone have been designed and synthesized. Chiral enynes derived from enantiomerically enriched homoallyl and homopropargyl alcohols were converted into bicyclic cyclopentenone structures by intramolecular Pauson-Khand reactions. This strategy provides a facile access to various bicyclic cyclopentenones substituted with benzofuran or benzothiophene ring systems in good yields. In addition to the experimental work, the ground state geometries of the hybrid compounds were optimized using Density Functional Theory applications at the B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.02.014