2-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]thiophene | 1242027-79-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]thiophene
• CAS: 1242027-79-7
• 化学式: C₁₆H₁₂OS₂
• 分子量: 284.403
• InChiKey: RBPIGWVAZXHZPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]thiophene 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 0.5h， 生成 2-(3,4-dimethylfuran-2-yl)thiophene
  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-thienyl-3-(phenylsulfanyl)propargyl alcohol 、 2-丙炔-1-醇 在 四丁基硫酸氢铵 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 、 水 为溶剂， 以50%的产率得到2-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]thiophene
  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

文献信息

• Copper-Catalyzed Complete Regio- and Stereoselective Cyclization of 1-Aryl-3-sulfanyl-4-oxahepta-1,6-diynes Triggered by Alkynylation
  作者：Mitsuhiro Yoshimatsu、Hitomi Sasaki、Yuko Sugimoto、Yuya Nagase、Genzoh Tanabe、Osamu Muraoka

  DOI：10.1021/ol3011453

  日期：2012.6.15

  Copper(I)-catalyzed alkynylation–cyclization of 4-oxahepta-1,6-diynes 1 with a wide variety of terminal alkynes proceeded to give (3E,4Z)-3-(phenylsulfanylmethylene)-4-(2-propynylidene)tetrahydrofuran-2-yl]benzenes 2aa–he in high yields with complete regio- and stereoselectivity.

  铜（I）催化的4-氧杂庚烷-1,6-二炔1与各种末端炔烃的炔基化环化反应产生（3 E，4 Z）-3-（苯硫基亚甲基）-4-（2-丙炔基） ）四氢呋喃-2-基]苯2AA -他以高收率和完整区域选择性和立体选择性。