2-(cyclohexylthio)-1-phenylethanone | 175434-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(cyclohexylthio)-1-phenylethanone
• 英文别名: Ethanone, 2-(cyclohexylthio)-1-phenyl-；2-cyclohexylsulfanyl-1-phenylethanone
• CAS: 175434-81-8
• 化学式: C₁₄H₁₈OS
• mdl: MFCD03963171
• 分子量: 234.362
• InChiKey: ICSZGYDRIQTLOV-UHFFFAOYSA-N

物化性质

• 沸点：
  153-155 °C(Press: 2 Torr)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-(cyclohexylthio)-1-phenylethanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以76%的产率得到2-(cyclohexylsulfonyl)-1-phenylethan-1-one
  参考文献：
  名称：

  Selectfluor™F–TEDA–BF 4对β-酮砜进行α-氟化

  摘要：

  使用Selectfluor™尝试对β-酮硫醚进行氟化，仅导致了相应的二芳基二硫化物的分离，推测是由于不稳定的氟化中间体的分解而引起的。但是，在无水条件下使用Selectfluor™对β-酮砜进行氟化，确实能够以中等到良好的产率分离出单氟化和二氟化的产物。

  DOI：

  10.1016/j.tet.2008.05.034
• 作为产物：
  描述：

  环己硫醇 、 2-溴苯乙酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-(cyclohexylthio)-1-phenylethanone
  参考文献：
  名称：

  取代苯甲酰基芳基/环己基硫化物的吡嗪衍生物及其抗分枝杆菌活性

  摘要：

  已经发现在N，N-二甲基甲酰胺中用过量的三氯氧化磷处理衍生自取代的苯甲酰基芳基/环己基硫化物的叠氮在每种情况下会产生两种异构的吡唑。已经提出了一种合理的机制来形成产物。已测试了同分异构化合物的抗分枝杆菌活性，可抵抗结核分枝杆菌（MTB）。

  DOI：

  10.1016/j.bmcl.2010.09.137

文献信息

• Selective one-pot multicomponent synthesis and anti-tubercular evaluation of 5-(aryl/cyclohexylsulfanyl)-2-alkoxy-4,6-diarylnicotinonitriles
  作者：Ramaiyan Manikannan、Shanmugam Muthusubramanian、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2010.04.025

  日期：2010.6

  A new set of highly substituted pyridine derivatives has been synthesized by a product selective four component reaction of aryl aldehyde, malononitrile and 2-aryl/cyclohexylsulfanyl-1-aryl-1-ethanones in presence of sodium hydroxide in methyl/ethyl alcohol. Among the compounds, 4,6-bis(4-chlorophenyl)-5-[(4-chlorophenyl)sulfanyl]-2-methoxynicotinonitrile (4n) inhibited Mycobacterium tuberculosis (MTB)

  通过在甲醇/乙醇中存在氢氧化钠的情况下，通过芳基醛，丙二腈和2-芳基/环己基硫烷基-1-芳基-乙酮的产物选择性四组分反应合成了一组新的高度取代的吡啶衍生物。在这些化合物中，4,6-双（4-氯苯基）-5-[（4-氯苯基）硫烷基] -2-甲氧基烟腈（4n）抑制结核分枝杆菌（MTB）的最小抑制浓度（MIC）为3.1μM，为比乙胺丁醇和吡嗪酰胺更有效。
• An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor™ F-TEDA-BF4
  作者：Mohammad Reza Poor Heravi

  DOI：10.1016/j.cclet.2010.06.030

  日期：2010.12

  The fluorination reaction involving a beta-ketosulfones by Selectfluor (TM) was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-beta-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation. (C) 2010 Mohammad Reza Poor Heravi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis and Conformational Features of 4-(Cyclohexylsulfanyl)-1-(2,4-dinitrophenyl)-3-aryl-1<i>H</i>-pyrazole
  作者：Ramaiyan Manikannan、Ramaiyan Venkatesan、Shanmugam Muthusubramanian

  DOI：10.1080/00397911.2010.493628

  日期：2011.7.1

  [image omitted] A set of new 4-(cyclohexylsulfanyl)-1,3-diaryl-1H-pyrazoles has been synthesized using Vilsmeier's reagent. It is found that 4-(cyclohexylsulfanyl)-1-(2,4-dinitrophenyl)-3-(4-methoxyphenyl)-1H-pyrazole exists with the arylthio group in the equatorial position of the cyclohexyl group in solution, whereas it has the arylthio group in the axial position of the cyclohexyl group in crystal state as evidenced by NMR and single-crystal x-ray analysis respectively.
• Saravanan, Sivaperuman; Namitharan, Kayambu; Muthusubramanian, Shanmugam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 305 - 309
  作者：Saravanan, Sivaperuman、Namitharan, Kayambu、Muthusubramanian, Shanmugam

  DOI：——

  日期：——
• Synthesis of Highly Substituted N-Hydroxy Piperidine via Intramolecular Reductive Cyclization of 1-Keto-5-ketoxime
  作者：Muthupandi Nagaraj、Muthusamy Boominathan、Ramaiyan Manikannan、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1080/00397911.2011.614715

  日期：2013.3.1

  Diasteroselective synthesis of highly substituted N-hydroxypiperidine was achieved by an intramolecular reductive cyclization of monoxime (2) of the 1,5-diketone (1), generated from 2-(cyclohexylthio)-1-phenylethanone and arylaldehyde, using NaBH3CN. The major product N-hydroxypiperidine (3) has been found to be racemate of a single diastereomer.