1-phenyl-3-(phenylthio)prop-2-yn-1-ol | 79894-59-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenyl-3-(phenylthio)prop-2-yn-1-ol
• 英文别名: 1-Phenyl-3-phenylsulfanylprop-2-yn-1-ol
• CAS: 79894-59-0
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: NGEROHQXHLTZPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(phenylthio)prop-2-yn-1-ol 在 N-碘代丁二酰亚胺 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 以93 %的产率得到(Z)-S-phenyl 2-iodo-3-phenylprop-2-enethioate
  参考文献：
  名称：

  银(I)催化的立体选择性Meyer-Schuster型重排：密集取代的α-碘α,β-不饱和硫酯的合成

  摘要：

  在此，我们报告了使用银 (I ) 催化剂和 N-碘代琥珀酰亚胺作为亲电子碘源。对于一系列炔丙基硫代炔，该反应顺利进行，从而以良好的收率生成三取代和四取代的烯烃，对于许多例子，(Z) -选择性。银催化剂可能发挥双重作用，包括通过亲炔银 (I) 激活 π 系统，并最终激活 NIS产生硫稳定的乙烯基阳离子/烯酮硫鎓中间体。这种反应性中间体被捕获在分子内，产生氧杂环丁烷，然后氧杂环丁烷很容易分解，得到最终产物。

  DOI：

  10.1039/d3nj05144g
• 作为产物：
  描述：

  phenylthioethynyl trimethylsilane 在 potassium fluoride 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 1.49h， 生成 1-phenyl-3-(phenylthio)prop-2-yn-1-ol
  参考文献：
  名称：

  Reactivity of Individual Organolithium Aggregates:  A RINMR Study of n-Butyllithium and 2-Methoxy-6-(methoxymethyl)phenyllithium

  摘要：

  Low-temperature rapid injection NMR (RINMR) experiments were performed on two lithium reagents, n-butyllithium and 2-methoxy-6-(methoxymethyl) phenyllithium ( 5), with the goal of measuring the relative reactivity of the different aggregates ( dimer, mixed dimer, and tetramer for n-BuLi, monomer and tetramer for 5) toward typical electrophiles. The reaction of the n-BuLi dimer with ( trimethylsilyl) acetylene first forms the mixed dimer n-(BuLiMe3SiC)-Me-. CLi, which is about 1/60 as reactive as the n-BuLi homodimer. The tetramer does not react. In the deprotonation of (phenylthio) acetylene, the n-BuLi dimer was found to be 3.5 x 10(8) as reactive as the tetramer, and in the addition to p-diethylaminobenzaldehyde, the relative reactivity was at least 2 x 10(4). In the deprotonation of (p-tolylsulfonyl) acetylene, the monomer of 5 was at least 1014 times as reactive as the tetramer. These measurements show that the difference in reactivity between the lower and higher aggregates of organolithium reagents can be many orders of magnitude higher than all previous estimates.

  DOI：

  10.1021/ja0689334

文献信息

• Facile one-pot synthesis of three different substituted thiazoles from propargylic alcohols
  作者：Xun Gao、Ying-ming Pan、Min Lin、Li Chen、Zhuang-ping Zhan

  DOI：10.1039/c002093a

  日期：——

  Three different substituted thiazoles have been successfully synthesized from readily available propargylic alcohols. Various secondary propargylic alcohols or tertiary propargylic alcohols participated well in the reaction, providing the desired products in good yields. This method provides a flexible and rapid route to substituted thiazoles.

  目前已成功地以易得的炔丙醇为原料合成了三种不同取代的噻唑。各种二级炔丙醇或三级炔丙醇均能很好地参与反应，提供了产率良好的目标产物。该方法为合成取代噻唑提供了一种灵活而快速的途径。
• 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。
• Highly Regioselective Hydrosilylation of Unsymmetric Alkynes Using a Phenylthio Directing Group
  作者：Kuan-Hsun Huang、Minoru Isobe

  DOI：10.1002/ejoc.201402577

  日期：2014.8

  Cobalt-assisted hydrosilylation of acetylenes is particularly interesting in organic synthesis since alkynyl group functionalization can give way to more useful substructures. This study aims to answer the general question of how to control hydrosilylation regioselectivity with unsymmetric alkynyl groups. Cobalt-catalyzed hydrosilylation is highly regioselective with alkyl-phenylthio-acetylenes affording

  乙炔的钴辅助氢化硅烷化在有机合成中特别有趣，因为炔基官能化可以让位于更有用的子结构。本研究旨在回答如何用不对称炔基控制氢化硅烷化区域选择性的一般问题。钴催化的氢化硅烷化对烷基苯硫基乙炔具有高度区域选择性，可提供相应的顺式-α-甲硅烷基-α-硫代芳基取代的烯烃。然而，在涉及具有相对较小烷基的底物的情况下，该反应失去区域选择性。该反应中的导向基团的作用是（i）对烷基施加空间效应，以及（ii）表达硫或氧原子的立体电子效应。
• 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。
• Scandium-Catalyzed Carbon−Carbon Bond-Forming Reactions of 3-Sulfanyl- and 3-Selanylpropargyl Alcohols
  作者：Mitsuhiro Yoshimatsu、Tokutaro Otani、Saki Matsuda、Teruhisa Yamamoto、Arisa Sawa

  DOI：10.1021/ol801533p

  日期：2008.10.2

  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.