3-(phenylselanyl)-1-(thiophen-2-yl)prop-2-yn-1-ol | 1062602-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(phenylselanyl)-1-(thiophen-2-yl)prop-2-yn-1-ol
• 英文别名: 3-(phenylselanyl)-1-(2-thienyl)prop-2-yn-1-ol；3-Phenylselanyl-1-thiophen-2-ylprop-2-yn-1-ol
• CAS: 1062602-46-3
• 化学式: C₁₃H₁₀OSSe
• 分子量: 293.248
• InChiKey: LPGOAUGRMNYCMD-UHFFFAOYSA-N

物化性质

• 沸点：
  436.4±55.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基噻吩 、 3-(phenylselanyl)-1-(thiophen-2-yl)prop-2-yn-1-ol 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 为溶剂， 以71%的产率得到5-methyl-2-[3-(phenylselanyl)-1-(2-thienyl)prop-2-yn-1-yl]thiophene
  参考文献：
  名称：

  Scandium-Catalyzed Carbon−Carbon Bond-Forming Reactions of 3-Sulfanyl- and 3-Selanylpropargyl Alcohols

  摘要：

  The scandium-catalyzed substitution reactions of the phenylsulfanyl and phenylselanyl propargyl alcohols 3a-i and 7a-h regioselectively proceeded to give the propargylated compounds 4 and 8 in high yields.

  DOI：

  10.1021/ol801533p
• 作为产物：
  描述：

  2-噻吩甲醛 、 ethynyl(phenyl)selane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以88%的产率得到3-(phenylselanyl)-1-(thiophen-2-yl)prop-2-yn-1-ol
  参考文献：
  名称：

  Scandium-Catalyzed Carbon−Carbon Bond-Forming Reactions of 3-Sulfanyl- and 3-Selanylpropargyl Alcohols

  摘要：

  The scandium-catalyzed substitution reactions of the phenylsulfanyl and phenylselanyl propargyl alcohols 3a-i and 7a-h regioselectively proceeded to give the propargylated compounds 4 and 8 in high yields.

  DOI：

  10.1021/ol801533p

文献信息

• 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。
• Synthesis of Thiazinoimidazoles by Lewis Acid-Catalyzed [3+3] Cycloaddition Reactions of Propargyl Alcohols with 2-Mercaptoimidazoles
  作者：Naoya Mishima、Takahiro Ogawa、Genzoh Tanabe、Osamu Muraoka、Hiroaki Wasada、Noriyuki Hatae、Mitsuhiro Yoshimatsu

  DOI：10.1002/ejoc.201900367

  日期：2019.6.2

  Fused thiazinoimidazole synthesis from the sulfur‐ and selenium‐substituted propargyl alcohols with 2‐mercaptoimidazoles were reported. The protocol is utilized for [3+3] annulation reactions of a wide variety of propargyl alcohols with three types of 2‐mercaptoimidazoles. The reactions were regioselective, atom economical, and versatile. Further transmetalation and the successive hydration and alkylation

  据报道，硫和硒取代的炔丙醇与2-巯基咪唑的熔融合成噻嗪基咪唑。该协议可用于多种炔丙醇与三种类型的2-巯基咪唑的[3 + 3]环化反应。反应是区域选择性的，原子经济的和通用的。进一步的重金属化以及连续的水合和烷基化可以提供更有用的噻嗪。
• 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.