1-methoxy-4-[4-(2-naphthoxymethyl)-3-(phenylsulfanylmethyl)-furan-2-yl]benzene | 1356384-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methoxy-4-[4-(2-naphthoxymethyl)-3-(phenylsulfanylmethyl)-furan-2-yl]benzene
• 英文别名: 2-(4-Methoxyphenyl)-4-(naphthalen-2-yloxymethyl)-3-(phenylsulfanylmethyl)furan；2-(4-methoxyphenyl)-4-(naphthalen-2-yloxymethyl)-3-(phenylsulfanylmethyl)furan
• CAS: 1356384-43-4
• 化学式: C₂₉H₂₄O₃S
• 分子量: 452.574
• InChiKey: VFMMSVGOZTWCDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methoxy-4-[4-(2-naphthoxymethyl)-3-(phenylsulfanylmethyl)-furan-2-yl]benzene 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60%的产率得到1-methoxy-4-[3-(2-naphthoxymethyl)-4-methylfuran-2-yl]benzene
  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-methoxy-4-[4-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene 、 sodium 2-naphtholate 以 1,4-二氧六环 为溶剂， 以64%的产率得到1-methoxy-4-[4-(2-naphthoxymethyl)-3-(phenylsulfanylmethyl)-furan-2-yl]benzene
  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

文献信息

• 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
  作者：Nami Takahashi、Yuya Nagase、Genzoh Tanabe、Osamu Muraoka、Mitsuhiro Yoshimatsu

  DOI：10.1016/j.tet.2011.11.096

  日期：2012.2

  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.