1-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-(phenylsulfanyl)prop-2-yn-1-ol | 1356384-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-(phenylsulfanyl)prop-2-yn-1-ol
• CAS: 1356384-85-4
• 化学式: C₂₀H₂₀O₂S
• 分子量: 324.444
• InChiKey: AODZVSSGFBGGMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-(phenylsulfanyl)prop-2-yn-1-ol 、 2-丙炔-1-醇 在 四丁基硫酸氢铵 、 lanthanum(lll) triflate 作用下， 以 硝基甲烷 、 水 为溶剂， 反应 1.0h， 以51%的产率得到5-methoxy-6-[1-propargyloxy-3-(phenylsulfanyl)prop-2-yn-1-yl]-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of 3-methyl- and 3,4-dimethylfurans using alkoxide, thiolate, and phenoxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing sulfur and selenium functional groups

  摘要：

  We have reported sodium alkoxide- or aryloxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing the phenylsulfanyl group 1a-d. The reactions with diverse sodium alkoxides and aryloxide produced 4-alkoxymethyl- and 4-aryloxymethylfurans 2aa-2db in good to high yields. Although reactions with sodium benzenethiolate yielded 3,4-bis(phenylsulfanylmethyl)furans 5a-g, they readily desulfanylated in the presence of tributyltin hydride/AIBN to give the 3-methyl- and 3,4-dimethylfuran derivatives 6a-g. This method's utility was demonstrated by the synthesis of tetrahydronaphthalenyl furan derivatives bearing alkoxy- and aryloxymethyl substituents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.096
• 作为产物：
  描述：

  乙炔基苯基硫醚 、 1-methoxy-5,6,7,8-tetrahydronaphth-2-yl aldehyde 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以92%的产率得到1-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-(phenylsulfanyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of 3-methyl- and 3,4-dimethylfurans using alkoxide, thiolate, and phenoxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing sulfur and selenium functional groups

  摘要：

  We have reported sodium alkoxide- or aryloxide-mediated cyclization of 4-oxahepta-1,6-diynes bearing the phenylsulfanyl group 1a-d. The reactions with diverse sodium alkoxides and aryloxide produced 4-alkoxymethyl- and 4-aryloxymethylfurans 2aa-2db in good to high yields. Although reactions with sodium benzenethiolate yielded 3,4-bis(phenylsulfanylmethyl)furans 5a-g, they readily desulfanylated in the presence of tributyltin hydride/AIBN to give the 3-methyl- and 3,4-dimethylfuran derivatives 6a-g. This method's utility was demonstrated by the synthesis of tetrahydronaphthalenyl furan derivatives bearing alkoxy- and aryloxymethyl substituents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.096