1-(1-naphthyl)-3-(phenylselenyl)prop-2-yn-1-ol | 1167412-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-naphthyl)-3-(phenylselenyl)prop-2-yn-1-ol
• CAS: 1167412-95-4
• 化学式: C₁₉H₁₄OSe
• 分子量: 337.28
• InChiKey: WHIPSJQBVDZZQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(1-naphthyl)-3-(phenylselenyl)prop-2-yn-1-ol 在 sodium methylate 、 四丁基硫酸氢铵 、 lanthanum(lll) triflate 作用下， 以 1,4-二氧六环 、 甲醇 、 硝基甲烷 、 水 为溶剂， 反应 1.0h， 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
• 作为产物：
  描述：

  ethynyl(phenyl)selane 、 1-萘甲醛 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 1-(1-naphthyl)-3-(phenylselenyl)prop-2-yn-1-ol
  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

• Lewis Acid-Catalyzed Propargylic Etherification and Sulfanylation from Alcohols in MeNO2-H2O
  作者：Katsuki Ohta、Eri Koketsu、Yuya Nagase、Nami Takahashi、Hiroyasu Watanabe、Mitsuhiro Yoshimatsu

  DOI：10.1248/cpb.59.1133

  日期：——

  Direct scandium- and lanthanum-catalyzed etherifications of propargyl alcohols 1 and 6 in MeNO2–H2O provided propargyl ethers 3, 4 and 7 in high yields. In addition, reactions of 1 and 6 with thiols exclusively yielded the corresponding propargyl sulfides.

  直接由钪和镧催化的丙炔醇1和6在甲基硝酸酯-水体系中的醚化反应，能够高效地生成丙炔醚3、4和7。此外，1和6与硫醇的反应则专门生成了相应的丙炔硫醚。
• α-Sulfanyl and α-Selanyl Propadienyl Cations: Regioselective Generations and Cycloadditions with Thioamides and Selemides Controlled by MeNO₂−H₂O System
  作者：Mitsuhiro Yoshimatsu、Teruhisa Yamamoto、Arisa Sawa、Tomohiro Kato、Genzoh Tanabe、Osamu Muraoka

  DOI：10.1021/ol9011844

  日期：2009.7.2

  α-Sulfanyl and α-selanyl propadienyl cations were easily generated by the catalytic system, scandium triflate-nitromethane-H2O in the presence of Bu4NHSO4, to regioselectively afford the multifunctionalized thiazoles and selenazoles in high yields.

  在Bu 4 NHSO 4的存在下，催化体系三氟甲磺酸-硝基甲烷-H 2 O易于生成α-硫烷基和α-硒代丙二烯基阳离子，从而以高收率选择性地提供了多官能化的噻唑和亚硒唑。
• Scandium-Catalyzed Propargylation of 1,3-Diketones with Propargyl Alcohols Bearing Sulfur or Selenium Functional Groups: Useful Transformation to Furans and Pyrans
  作者：Katsuki Ohta、Taira Kobayashi、Genzoh Tanabe、Osamu Muraoka、Mitsuhiro Yoshimatsu

  DOI：10.1248/cpb.58.1180

  日期：——

  Propargylations of 1,3-diketones using 3-sulfanyl and 3-selanylpropargyl alcohols 1 in MeNO2–H2O gave alkynyl ketones 2a—m, 2o—v and 6,7-dihydro-5H-cyclohexa[b]pyran-5-ones 3k—n. With some bases, the useful propargylated 1,3-diketones underwent intramolecular cyclization to give 6,7-dihydro-5H-benzofuran-4-ones 4a—i or 4,5,6,7-tetrahydrobenzofurans 5p, 6p—v.

  使用3-硫基和3-硒基丙炔醇1在MeNO2-H2O中对1,3-二酮进行丙炔化反应，得到了烷炔酮2a—m、2o—v以及6,7-二氢-5H-环己[b]吡喃-5-酮3k—n。与一些碱反应时，有效的丙炔化1,3-二酮发生分子内环化，生成6,7-二氢-5H-苯并呋喃-4-酮4a—i或4,5,6,7-四氢苯并呋喃5p、6p—v。