2-Methyl-2-phenylthio-cyclohexanon | 54376-46-4

• 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-Methyl-2-phenylthio-cyclohexanon
• 英文别名: 2-Methyl-2-phenylthiocyclohexanone；2-Methyl-2-(phenylsulfanyl)cyclohexanone；2-methyl-2-phenylsulfanylcyclohexan-1-one
• CAS: 54376-46-4
• 化学式: C₁₃H₁₆OS
• 分子量: 220.335
• InChiKey: BKWNNSJZBGLZHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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-Methyl-2-phenylthio-cyclohexanon 在 三乙胺 作用下， 以 乙二醇二甲醚 、 苯 为溶剂， 生成 1-Methyl-3-phenylthio-2-trimethylsilyloxy-1-cyclohexen
  参考文献：
  名称：

  三甲基甲硅烷基-烯醇式乙烯，α-二烷基-α-苯硫基酮中的苯甲基硫脲的Umlagerungen der Phenylthiogruppe

  摘要：

  α，α-二烷基化的α-苯硫基酮的三甲基甲硅烷基烯醇的苯硫基的重排

  DOI：

  10.1002/hlca.19780610108
• 作为产物：
  描述：

  1-(1-phenylsulfanylvinyl)cyclopentanol 在 gold(I) chloride 作用下， 以 硝基甲烷 为溶剂， 以109 mg的产率得到2-Methyl-2-phenylthio-cyclohexanon
  参考文献：
  名称：

  One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions

  摘要：

  An atom-efficient synthesis of keto thioethers was devised via tandem gold/palladium catalysis. The reaction proceeds through a regioselective thiol attack at the beta-position of the alcohol, followed by an alkyl, aryl, or benzyl 1,2-shift. Both acyclic and cyclic systems were studied, in the latter case leading to the ring expansion of cyclic substrates.

  DOI：

  10.1021/ol502553p

文献信息

• 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。
• Thiosulfonic<i>S</i>-Esters; 6. Fluoride-Mediated α-Phenylsulfenylation of Cyclic Ketones and Esters via their Trimethylsilyl Enol Ethers
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo

  DOI：10.1055/s-1989-27292

  日期：——

  Ketones and carboxylic acid esters are conveniently converted to their α-sulfenylated derivatives. This new procedure is likely to represent the first reliable one for regiospecific monosulfenylation of carbonyl compounds. It is based on the reaction of their trimethylsilyl enol ether derivatives with tetrabutylammonium fluoride in the presence of thiosulfonic S-esters, in anhydrous tetrahydrofuran, under mild conditions, at - 70°C for a few minutes.

  酮和羧酸酯可方便地转化为它们的α-亚磺酰化衍生物。这一新方法可能代表了首个可靠的、针对羰基化合物进行区域选择性单亚磺酰化的方法。其基础是：在无水四氢呋喃中，在温和条件下，以-70°C温度持续几分钟，利用三甲基硅基烯醇醚衍生物与四丁基氟化铵在硫代磺酸S-酯存在下反应。
• New mild methodology for the synthesis of α-phenylthio and α-phenylseleno ketones
  作者：Philip Magnus、Pascal Rigollier

  DOI：10.1016/s0040-4039(00)60019-9

  日期：1992.10

  Treatment of trimethylsilyl enol ethers with the adduct 1, derived from chloramine-T and (PhS)2, gave good yields of alpha-phenylthioketones. The selenium version of this reagent 2 gave alpha-phenylselenoketones.
• Tanaka; Azuma; Fang, Synlett, 2000, # 1, p. 33 - 36
  作者：Tanaka、Azuma、Fang、Uchida、Iwata、Ishida、In、Maezaki

  DOI：——

  日期：——
• New synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketones
  作者：Barry M. Trost、Thomas N. Salzmann、Kunio Hiroi

  DOI：10.1021/ja00432a034

  日期：1976.8