1-[3,4-bis(phenylsulfanylmethyl)furan-2-yl]naphthalene | 1356384-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[3,4-bis(phenylsulfanylmethyl)furan-2-yl]naphthalene
• CAS: 1356384-67-2
• 化学式: C₂₈H₂₂OS₂
• 分子量: 438.614
• InChiKey: BRSQZCHMVLXASG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[3,4-bis(phenylsulfanylmethyl)furan-2-yl]naphthalene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以79%的产率得到1-(3,4-dimethylfuran-2-yl)naphthalene
  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：

  1-萘甲醛 在 正丁基锂 、 sodium methylate 、 四丁基硫酸氢铵 、 lanthanum(lll) triflate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 硝基甲烷 、 正己烷 、 水 为溶剂， 反应 1.67h， 生成 1-[3,4-bis(phenylsulfanylmethyl)furan-2-yl]naphthalene
  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