4-(phenylthio)-3-buten-1-ol | 221033-16-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(phenylthio)-3-buten-1-ol
• 英文别名: 4-phenylsulfanylbut-3-en-1-ol
• CAS: 221033-16-5
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: PWXMYZKZMIDKGY-UHFFFAOYSA-N

物化性质

• 沸点：
  313.3±34.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(phenylthio)-3-buten-1-ol 在 吡啶 、 高氯酸铵 、 (1,4,8,11-tetraazacyclotetradecane)nickel(II) perchlorate 、 高氯酸四乙基铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (1E and 1Z)-4-acetoxy-1-(phenylthio)-1-butene
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  tert-butyldimethyl(4-(phenylthio)but-3-enyloxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 4-(phenylthio)-3-buten-1-ol
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e

文献信息

• Et₃B Induced Radical Addition of Thiols to Acetylenes
  作者：Yoshifumi Ichinose、Kuni Wakamatsu、Kyoko Nozaki、Jean-Luc Birbaum、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/cl.1987.1647

  日期：1987.8.5

  Thiols added easily to acetylenic compounds in the presence of Et3B to give alkenyl sulfides in good yields. The reaction of acetylenes with 3-methyl-2-buten-1-thio1 gave dihydro-thiophene derivatives in one pot.

  在 Et3B 存在下，硫醇很容易添加到乙炔化合物中，从而以良好的收率得到烯基硫化物。乙炔与 3-methyl-2-buten-1-thio1 的反应在一锅中得到二氢噻吩衍生物。
• Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries
  作者：Shishi Lin、Shane D. Lies、Christopher S. Gravatt、Tehshik P. Yoon

  DOI：10.1021/acs.orglett.6b03545

  日期：2017.1.20

  The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach

  易于氧化的芳基硫醚部分的引入促进了烯烃自由基阳离子的光催化生成，该自由基阳离子与富电子反应伙伴进行各种环加成反应。随后，硫化物部分可以以无痕方式还原裂解，从而提供使用光氧化还原催化无法直接获得的产物。这种方法构成了一种新颖的氧化“氧化还原辅助”策略，提供了一种实用的方法来规避光氧化还原反应面临的基本热力学限制。
• Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenols using a water-soluble radical initiator in water. A facile synthesis of γ-lactones
  作者：Hideki Yorimitsu、Katsuyu Wakabayashi、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1016/s0040-4039(98)02391-0

  日期：1999.1

  of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis(4-cyanopentanoic acid), provided γ-(4-hydroxybutyl)-γ-lactone in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93 % yield.

  在水溶性自由基引发剂4,4'-偶氮双（4-氰基戊酸）存在下于75°C在水中加热2-碘乙酰胺和5-hexen-1-ol的混合物，得到γ-（4 -羟基丁）-γ-内酯，产率为95％。用2-碘乙酸代替2-碘乙酰胺也以93％的产率得到了相同的γ-内酯。
• Radical Addition of 2-Iodoalkanamide or 2-Iodoalkanoic Acid to Alkenes with a Water-Soluble Radical Initiator in Aqueous Media: Facile Synthesis of<i>γ</i>-Lactones
  作者：Hideki Yorimitsu、Katsuyu Wakabayashi、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1246/bcsj.74.1963

  日期：2001.10

  Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis(4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.

  在水或含水乙醇中使用水溶性自由基引发剂的剧烈反应已有报道。将2-碘代乙酰胺和5-己烯-1-醇的混合物在75°C下加热，并加入水溶性自由基引发剂4,4′-偶氮双（4-氰基戊酸），可得到产率为95%的5-（4-羟基丁基）二氢呋喃-2（3H）-酮。使用2-碘代乙酸代替2-碘代乙酰胺也能以93%的产率得到相同的γ-内酯。在含水乙醇中，通过2,2′-偶氮双（2-甲基丙酰胺）二盐酸盐引发2-碘代乙酰胺与1-辛烯的反应，得到γ-癸醇内酯。使用水作为溶剂对于获得高产率的乳酮至关重要。
• 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.