5-[3,4-bis(phenylsulfanylmethyl)-2-furyl]-1,3-benzodioxole | 1242027-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-[3,4-bis(phenylsulfanylmethyl)-2-furyl]-1,3-benzodioxole
• 英文别名: 5-[3,4-Bis(phenylsulfanylmethyl)furan-2-yl]-1,3-benzodioxole；5-[3,4-bis(phenylsulfanylmethyl)furan-2-yl]-1,3-benzodioxole
• CAS: 1242027-92-4
• 化学式: C₂₅H₂₀O₃S₂
• 分子量: 432.564
• InChiKey: BVRBBEDUFBFWHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[3,4-bis(phenylsulfanylmethyl)-2-furyl]-1,3-benzodioxole 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以65%的产率得到5-(3,4-dimethyl-2-furyl)-1,3-benzodioxole
  参考文献：
  名称：

  New Cyclization of 4-Oxahepta-1,6-diynes Bearing Sulfur and Selenium Functional Groups

  摘要：

  New cyclizations of 1-sulfanyl- and -selany1-4-oxa-1,6-heptadiynes using sodium alkoxide or thiolates provided 4-alkoxymethy1-3-phenylsulfanyl- and 3,4-bis(sulfanylmethyl)furans in high yields.

  DOI：

  10.1021/ol101540s
• 作为产物：
  描述：

  5-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzodioxole 、 sodium thiophenolate 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 以99%的产率得到5-[3,4-bis(phenylsulfanylmethyl)-2-furyl]-1,3-benzodioxole
  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

• New Cyclization of 4-Oxahepta-1,6-diynes Bearing Sulfur and Selenium Functional Groups
  作者：Mitsuhiro Yoshimatsu、Hiroyasu Watanabe、Eri Koketsu

  DOI：10.1021/ol101540s

  日期：2010.9.17

  New cyclizations of 1-sulfanyl- and -selany1-4-oxa-1,6-heptadiynes using sodium alkoxide or thiolates provided 4-alkoxymethy1-3-phenylsulfanyl- and 3,4-bis(sulfanylmethyl)furans in high yields.
• 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.