2-甲基-2-苯基硫代环戊酮 | 35875-01-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-甲基-2-苯基硫代环戊酮
• 英文名称: 2-methyl-2-(phenylthio)cyclopentan-1-one
• 英文别名: 2-Methyl-2-phenylthiocyclopentanone；2-Methyl-2-(phenylthio)-cyclopentanon；2-Methyl-2-phenylthiocyclopentanon；2-Methyl-2-phenylsulfanylcyclopentan-1-one
• CAS: 35875-01-5
• 化学式: C₁₂H₁₄OS
• 分子量: 206.309
• InChiKey: YLWTYIIHGPPXJE-UHFFFAOYSA-N

物化性质

• 沸点：
  327.6±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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-甲基-2-苯基硫代环戊酮 、 氢化铝锂 生成 (1R,2R)-2-methyl-2-phenylsulfanylcyclopentan-1-ol
  参考文献：
  名称：

  WELCH, J. T.;ESWARAKRISHNAN, SEETHA, J. ORG. CHEM., 1985, 50, N 26, 5909-5910

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基-2-氧代环戊烷羧酸甲酯 以49%的产率得到
  参考文献：
  名称：

  ASAOKA M.; MIYAKE K.; TAKEI H., BULL. CHEM. SOC. JAP., 1978, 51, NO 10, 3008-3010

  摘要：

  DOI：

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。
• Sulfenylation Accompanied by Dealkoxycarbonylation of β-Keto Esters, Geminal Diesters, and α-Cyano Ester in Hexamethylphosphoric Triamide (HMPA)
  作者：Morio Asaoka、Kazutoshi Miyake、Hisashi Takei

  DOI：10.1246/bcsj.51.3008

  日期：1978.10

  In the presence of sodium iodide, diphenyl disulfide reacted with geminal diesters, β-keto esters, and α-cyano esters in hexamethylphosphoric triamide (HMPA) at 150–160 °C to give alkyl phenyl sulfides and α-phenylthio esters, ketones, and nitriles, respectively, along with evolution of carbon dioxide.

  在碘化钠存在下，二苯基二硫化物在 150-160 °C 的温度下与六甲基三磷酰胺 (HMPA) 中的宝石二酯、β-酮酯和α-氰酯发生反应，分别生成烷基苯基硫化物和α-苯基硫代酯、酮和腈，同时产生二氧化碳。
• One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions
  作者：Alban Cadu、Rahul A. Watile、Srijit Biswas、Andreas Orthaber、Per J. R. Sjöberg、Joseph S. M. Samec

  DOI：10.1021/ol502553p

  日期：2014.11.7

  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.
• Hannaby, Malcolm; Judson, Philip; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1992, # 20, p. 2609 - 2614
  作者：Hannaby, Malcolm、Judson, Philip、Warren, Stuart

  DOI：——

  日期：——
• Rearrangement of cyclic alcohols with an adjacent phenylthio (PhS-) group: Migration of a PhS group around a ring
  作者：Malcolm Hannaby、Stuart Warren

  DOI：10.1016/s0040-4039(00)84095-2

  日期：1986.1