2-phenylthio-4-methylcyclohexanone | 35985-28-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenylthio-4-methylcyclohexanone
• 英文别名: 4-Methyl-2-(phenylsulfanyl)cyclohexanone；4-methyl-2-phenylsulfanylcyclohexan-1-one
• CAS: 35985-28-5
• 化学式: C₁₃H₁₆OS
• 分子量: 220.335
• InChiKey: JQVIKAOAHLGSBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-phenylthio-4-methylcyclohexanone 在 吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 氧气 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 2-phenylthio-5-methyl-cyclohexanone
  参考文献：
  名称：

  在硫酚存在下通过氧合将链烯基硫化物区域特异性转化为α-磺酰化羰基化合物

  摘要：

  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。

  DOI：

  10.1039/c39880001468
• 作为产物：
  描述：

  4-甲基-1-(1-哌啶基)环己烯 、 N-(苯硫基)邻苯二甲酰亚胺 生成 2-phenylthio-4-methylcyclohexanone
  参考文献：
  名称：

  活性亚甲基化合物与磺胺的磺酰化

  摘要：

  衍生自仲烷基胺的次磺酰胺与活性亚甲基化合物的等摩尔反应以良好的产率提供单次磺酰化的化合物。2 mol 衍生自酰亚胺的次磺酰胺与 1 mol 活性亚甲基化合物在碱存在下反应，得到二亚磺酰化化合物。发现α-单-亚磺酰化酮是通过烯胺与衍生自酰亚胺的次磺酰胺反应制备的。α-gem-Di-sulfenylated 酮是通过 α-mono-sulfenylated 酮与衍生自酰亚胺的亚磺酰胺在碱存在下反应制备的。还研究了N-苯基硫代苯甲脒盐酸盐的制备和反应。

  DOI：

  10.1246/bcsj.45.866

文献信息

• Efficient and Stereoselective Synthesis of Bicyclo[3.2.1]octan-8-ones: Synthesis and Palladium-Catalyzed Isomerization of Functionalized 2-Vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans
  作者：Peter Langer、Edith Holtz、Nehad N. R. Saleh

  DOI：10.1002/1521-3765(20020215)8:4<917::aid-chem917>3.0.co;2-1

  日期：2002.2.15

  diastereoselective formation of 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans. The products could be efficiently transformed into functionalized bicyclo[3.2.1]octan-8-ones by a palladium-catalyzed rearrangement reaction. In case of sulfone derivatives, this rearrangement proceeds with high stereospecifity to give exclusively the endo-configured diastereomers. The bicyclo[3.2.1]octane skeleton is present

  据报道，用1,4-二溴-2-丁烯将二锂化的环状β-酮酯和β-酮砜进行新的C，O-环二烷基化反应会导致区域选择性和非对映选择性形成2-乙烯基-2,3,3a， 4,5,6-六氢-2,3-苯并呋喃。该产物可以通过钯催化的重排反应有效地转化为官能化的双环[3.2.1] octan-8-one。在砜衍生物的情况下，该重排以高立体特异性进行，以仅给出内构型的非对映异构体。双环[3.2.1]辛烷骨架存在于许多重要的药理天然产物中。
• 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.
• YOSHIDA, JUN-ICHI;NAKATANI, SHOGO;ISOE, SACHIHIKO, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 22, C. 1468-1470
  作者：YOSHIDA, JUN-ICHI、NAKATANI, SHOGO、ISOE, SACHIHIKO

  DOI：——

  日期：——
• Sulfenylation of Active Methylene Compounds with Sulfenamides
  作者：Takanobu Kumamoto、Susumu Kobayashi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.45.866

  日期：1972.3

  secondary alkylamines with active methylene compounds afforded mono-sulfenylated compounds in good yields. The reactions of 2 mol of sulfenamides derived from imides with 1 mol of active methylene compounds in the presence of a base gave di-sulfenylated compounds. It was found that α-mono-sulfenylated ketones were prepared by the reactions of enamines with sulfenamides derived from imides. α-gem-Di-sulfenylated

  衍生自仲烷基胺的次磺酰胺与活性亚甲基化合物的等摩尔反应以良好的产率提供单次磺酰化的化合物。2 mol 衍生自酰亚胺的次磺酰胺与 1 mol 活性亚甲基化合物在碱存在下反应，得到二亚磺酰化化合物。发现α-单-亚磺酰化酮是通过烯胺与衍生自酰亚胺的次磺酰胺反应制备的。α-gem-Di-sulfenylated 酮是通过 α-mono-sulfenylated 酮与衍生自酰亚胺的亚磺酰胺在碱存在下反应制备的。还研究了N-苯基硫代苯甲脒盐酸盐的制备和反应。
• 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。