((4aS,6R,7S,9aR)-6-(phenylthio)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-yloxy)-tert-butyldimethylsilane | 1016169-01-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ((4aS,6R,7S,9aR)-6-(phenylthio)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-yloxy)-tert-butyldimethylsilane
• CAS: 1016169-01-9
• 化学式: C₂₁H₃₂O₃SSi
• 分子量: 392.635
• InChiKey: RBBLCUOPVIOMIT-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((4aS,6R,7S,9aR)-6-(phenylthio)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-yloxy)-tert-butyldimethylsilane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.4h， 以89%的产率得到((4aS,6R,7S,9aR)-6-benzenesulfonyl-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-yloxy)-tert-butyldimethylsilane
  参考文献：
  名称：

  Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins

  摘要：

  An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use of a combination of allyltrimethylsilane and TiCl4 with 6-fluoro-7-hydroxytetrahydrooxepin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.018
• 作为产物：
  描述：

  ((1R,2S)-1-(phenylthio)-1-((2R,3S)-2-vinyltetrahydro-2H-pyran-3-yloxy)but-3-en-2-yloxy)-tert-butyldimethylsilane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以72%的产率得到((4aS,6R,7S,9aR)-6-(phenylthio)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-yloxy)-tert-butyldimethylsilane
  参考文献：
  名称：

  Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins

  摘要：

  An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use of a combination of allyltrimethylsilane and TiCl4 with 6-fluoro-7-hydroxytetrahydrooxepin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.018