1-fluoro-4-[4-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene | 1356384-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-fluoro-4-[4-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene
• 英文别名: 1-fluoro-4-[1-(propargyloxy)-3-(phenylsulfanyl)prop-2-yn-1-yl]benzene；1-Fluoro-4-(3-phenylsulfanyl-1-prop-2-ynoxyprop-2-ynyl)benzene
• CAS: 1356384-21-8
• 化学式: C₁₈H₁₃FOS
• 分子量: 296.365
• InChiKey: UDHCMTGFNZTCMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-fluoro-4-[4-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene 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 4-(4-methyl-3-phenylsulfanylmethylfuran-2-yl)-1-fluorobenzene
  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-(4-fluorophenyl)-3-(phenylthio)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76%的产率得到1-fluoro-4-[4-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-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

• 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。
• Ni–Pd Catalyzed Cyclization of Sulfanyl 1,6-Diynes: Synthesis of 1′-Homonucleoside Analogues
  作者：Yuka Kobayashi、Rena Tanahashi、Yui Yamaguchi、Noriyuki Hatae、Masanori Kobayashi、Yoshihito Ueno、Mitsuhiro Yoshimatsu

  DOI：10.1021/acs.joc.6b02841

  日期：2017.3.3

  The Ni–Pd catalyzed addition–cyclization of sulfanyl 1,6-diynes 2–9 with nucleobases is described. The reactions of N-tethered 1,6-diynes with N3-benzoylthymine, N4,N4-bis(Boc)cytosine, N3-benzoyluracil and N6,N6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with acids or bases. Furthermore

  在Ni-Pd催化硫烷基-1,6-二炔的加成环化2 - 9与核碱基进行说明。的反应Ñ -tethered -1,6-二炔与Ñ 3 -benzoylthymine，Ñ 4，Ñ 4双（BOC）胞嘧啶，Ñ 3 -benzoyluracil和Ñ 6，Ñ 6-双（Boc）腺嘌呤以良好的产率专门提供了吡咯基甲基和呋喃基甲基核苷酸。核碱基的脱保护通过用酸或碱处理完成。此外，吡咯和呋喃与亲核试剂如醇盐和胺的反应进行了脱甲苯基反应，并以良好的产率转化为烷氧基甲基和芳基氨基甲基-吡咯和呋喃。