3-(phenylthio)but-3-en-1-ol | 109553-20-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)but-3-en-1-ol
• 英文别名: 3-phenylthio-3-butenol；3-(Phenylsulfanyl)but-3-en-1-ol；3-phenylsulfanylbut-3-en-1-ol
• CAS: 109553-20-0
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: RALBLXHAMFTZGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-(phenylthio)but-3-en-1-ol 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.0h， 生成 N-benzyl-N'-(dodec-1-ynyl)-2-nitro-N'-(3-(phenylsulfonyl)but-3-enyl)benzenesulfonohydrazide
  参考文献：
  名称：

  Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes

  摘要：

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.

  DOI：

  10.1021/acs.orglett.7b02624
• 作为产物：
  描述：

  苯硫酚 、 3-丁炔-1-醇 在 bis(acetylacetonate)nickel(II) 作用下， 反应 2.0h， 以81%的产率得到3-(phenylthio)but-3-en-1-ol
  参考文献：
  名称：

  镍催化苯硫醇加成到炔烃：碳硫和碳碳键的形成

  摘要：

  镍催化苯硫醇与炔烃的加成生成烯基和二烯基硫化物；该过程的方向可以通过改变 PhSH/炔烃的比例来控制。一种确保 2-苯基硫烷基烯烃更高产率的先进程序包括将炔烃逐渐添加到其他反应物中。反应中形成的共轭二烯基硫醚的结构由二维核磁共振光谱确定。

  DOI：

  10.1007/s11172-006-0557-8

文献信息

• Synthesis of vinyl sulfides using glycerol as a recyclable solvent
  作者：Eder J. Lenardão、Márcio S. Silva、Renata G. Lara、Júnior M. Marczewski、Maraisa Sachini、Raquel G. Jacob、Diego Alves、Gelson Perin

  DOI：10.3998/ark.5550190.0012.222

  日期：——

  alkynes promoted by KF/Al2O3, using glycerol as recyclable solvent. This improved method furnishes selectively the corresponding anti-Markovnikov vinyl sulfides in good to excellent yields starting from terminal alkynes and aliphatic or aromatic thiols. The irradiation with microwaves facilitated the procedure and accelerates the reaction. The catalytic system and the glycerol can be re-used up to four

  描述了一种新的、清洁的、有效的协议，用于由 KF/Al2O3 促进的末端炔烃的氢硫醇化，使用甘油作为可回收溶剂。这种改进的方法从末端炔烃和脂肪族或芳香族硫醇开始，选择性地提供相应的反马尔科夫尼科夫乙烯基硫化物，产率良好至极好。微波辐射促进了该过程并加速了反应。催化系统和甘油可以重复使用多达四次，无需事先处理，并且具有相当的活性。
• A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines
  作者：Albert Padwa、Michael A. Brodney、Bing Liu、Kyosuke Satake、Tianhua Wu

  DOI：10.1021/jo982453g

  日期：1999.5.1

  acyl azide by a Curtius rearrangement in the presence of an alcohol. Alkylation of the resulting N-alkyl carbamate with an alkenyl bromide allows for the synthesis of a wide variety of cycloaddition precursors. The scope of the IMDAF reaction was evaluated by using mono- and disubstituted alkenes, electron rich and electron deficient olefins, and acetylenic tethers. Cyclic 2-amidofurans were also synthesized

  2-取代的氨基呋喃的分子内Diels-Alder反应（IMDAF）导致形成各种二氢吲哚和四氢喹啉。这些环系统从IMDAF反应中的分离可以根据最初的[4 + 2]-环加成反应进行合理化，该加成反应首先会生成一个oxa桥联的环加合物，由于它很容易进行氮辅助开环，因此未被发现。质子交换，然后最终脱水，得到芳族产物。在某些情况下，可以分离中间体环己二烯醇，并以高收率独立地转化为最终产物。起始2-氨基呋喃很容易在醇存在下通过Curtius重排由呋喃酰基酰基叠氮化物制备。所得的氨基甲酸N-烷基酯与烯基溴的烷基化可以合成多种环加成的前体。IMDAF反应的范围通过使用单取代和双取代的烯烃，富电子和缺电子的烯烃以及炔属系链进行评估。环状2-酰胺基呋喃还使用2-酰胺基取代的恶唑的相关分子内Diels-Alder反应合成，所述2-酰胺基取代的恶唑包含拴系的炔烃。这种转变代表了通往这种稀有杂环系统的新途径。顺序环
• A novel self-terminated Prins strategy for the synthesis of tetrahydropyran-4-one derivatives and their behaviour in Fisher indole synthesis
  作者：B. V. Subba Reddy、S. Rehana Anjum、B. Sridhar

  DOI：10.1039/c6ra11218h

  日期：——

  has been developed for the synthesis of 2-substituted tetrahydropyran-4-one derivatives through a condensation of 3-(phenylthio)but-3-en-1-ol with carbonyl compounds in the presence of 5 mol% of Sc(OTf)3 under mild conditions. A few products were subsequently transformed into the corresponding indoles by Fisher-indole synthesis.

  已开发出一种新颖的自封端Prins策略，用于在5 mol存在下通过3-（苯硫基）but-3-en-1-醇与羰基化合物的缩合反应合成2-取代的四氢吡喃-4-酮衍生物。在温和条件下的Sc（OTf）3的百分比。随后通过费希尔-吲哚合成将一些产物转化为相应的吲哚。
• Synthesis of vinyl sulfides via hydrothiolation of alkynes using Al2O3/KF under solvent-free conditions
  作者：Márcio S. Silva、Renata G. Lara、Júnior M. Marczewski、Raquel G. Jacob、Eder J. Lenardão、Gelson Perin

  DOI：10.1016/j.tetlet.2008.01.093

  日期：2008.3

  We present here a clean, solvent-free hydrothiolation of alkynes using solid supported catalyst (Al(2)O(3)/KF). This efficient and improved method selectively furnishes the corresponding anti-Markovnikov vinyl sulfides in good to excellent yields. The method is applicable for aliphatic and aromatic thiols and the catalytic system can be re-used up to two times without previous treatment and with comparable activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of vinyl sulfides under base-free conditions using selenium ionic liquid
  作者：Samuel Thurow、Naiana T. Ostosi、Samuel R. Mendes、Raquel G. Jacob、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2012.03.076

  日期：2012.5

  A very simple procedure is described for the efficient synthesis of vinyl sulfides by hydrothiolation of terminal alkynes using 1-n-butyl-3-methylimidazolium methylselenite, [bmim][SeO2(OCH3)]. The reaction proceeds cleanly under mild, base-free conditions and was performed with aromatic and aliphatic thiols. (C) 2012 Elsevier Ltd. All rights reserved.