4-Phenyl-2-(phenylthio)butanal | 121033-27-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-Phenyl-2-(phenylthio)butanal
• 英文别名: 4-Phenyl-2-phenylsulfanylbutanal
• CAS: 121033-27-0
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: CMQOUMFECWFTIA-UHFFFAOYSA-N

物化性质

• 沸点：
  385.7±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Phenyl-2-(phenylthio)butanal 在 镍 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 以81%的产率得到4-苯基丁醛
  参考文献：
  名称：

  一种由一碳原子延伸的醛合成α-硫代醛和醇的新方法

  摘要：

  通过使用氯甲基苯基亚砜作为一碳均质剂，实现了一种由一碳延伸率的醛类合成α-硫代醛的两步高效方法。α-硫代醛易于与Bu 3 SnH和AIBN在回流的苯中转化为脱硫醇，收率很高。

  DOI：

  10.1016/s0040-4039(00)00087-3
• 作为产物：
  描述：

  1-Methoxy-4-phenyl-1-phenylsulfanyl-butan-2-ol 在 甲基磺酰氯 、 三乙胺 作用下， 以 苯 为溶剂， 生成 4-Phenyl-2-(phenylthio)butanal
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c

文献信息

• Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds by oxygenation in the presence of thiophenol
  作者：Jun-ichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1039/c39880001468

  日期：——

  Regiospecific conversion of alkenyl sulphides to α-sulphenylated carbonyl compounds was achieved by oxygenation in the presence of thiophenol; electrolysis was found to be quite effective for initiation of the reaction.

  在硫酚的存在下，通过氧化实现烯基硫的区域特异性转化为α-磺苯基化的羰基化合物。发现电解对于引发反应是非常有效的。
• Air Oxidative Radical Oxysulfurization of Alkynes Leading to α-Thioaldehydes
  作者：Shao-Fang Zhou、Xiang-Qiang Pan、Zhi-Hao Zhou、Adedamola Shoberu、Pei-Zhi Zhang、Jian-Ping Zou

  DOI：10.1021/acs.joc.5b00641

  日期：2015.5.15

  Air oxidative radical oxysulfurization of alkynes initiated by 0.5 mol % tert-butyl hydroperoxide with arylthiols is described. The reaction proceeded at room temperature in the presence of 5% mol water to afford selective a-thioaldehydes.
• Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol
  作者：Junichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1021/jo00070a021

  日期：1993.8

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.
• A new method for the synthesis of α-thio aldehydes and alcohols from aldehydes with one-carbon elongation
  作者：Tsuyoshi Satoh、Ko-ichi Kubota

  DOI：10.1016/s0040-4039(00)00087-3

  日期：2000.3

  A two-step and high-yield method for the synthesis of α-thio aldehydes from aldehydes with one-carbon elongation is realized by using chloromethyl phenyl sulfoxide as a one-carbon homologating agent. The α-thio aldehydes are easily converted to desulfurized alcohols with Bu3SnH and AIBN in refluxing benzene in good yield.

  通过使用氯甲基苯基亚砜作为一碳均质剂，实现了一种由一碳延伸率的醛类合成α-硫代醛的两步高效方法。α-硫代醛易于与Bu 3 SnH和AIBN在回流的苯中转化为脱硫醇，收率很高。
• Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation
  作者：Veejendra K. Yadav、K. Ganesh Babu、Masood Parvez

  DOI：10.1021/jo034608c

  日期：2004.5.1

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.