2-(Cyclohexyl-phenylsulfanyl-methyl)-3-hydroxy-cyclohex-2-enone | 154876-45-6

• 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-(Cyclohexyl-phenylsulfanyl-methyl)-3-hydroxy-cyclohex-2-enone
• 英文别名: 2-[Cyclohexyl(phenylsulfanyl)methyl]-3-hydroxy-2-cyclohexen-1-one；2-[cyclohexyl(phenylsulfanyl)methyl]-3-hydroxycyclohex-2-en-1-one
• CAS: 154876-45-6
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: JLGZYHZHMKGONM-UHFFFAOYSA-N

物化性质

• 沸点：
  470.435±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.181±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Cyclohexyl-phenylsulfanyl-methyl)-3-hydroxy-cyclohex-2-enone 在 sodium periodate 、 氧气 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 8a-hydroxy-6,7,8,8a-tetrahydro-5H-spiro[benzo[c][1,2]dioxine-3,1'-cyclohexan]-5-one
  参考文献：
  名称：

  Access to Protected 2-Alkylidene 1,3-diones by Modified Knoevenagel Reaction in the Presence of Thiophenol. A New Approach to Spirocyclopentanol Construction

  摘要：

  A general procedure is described for trapping the products of Knoevenagel condensation involving 1,3-diketones and aliphatic aldehydes. Simple stirring of a three-component mixture consisting of each reactant and thiophenol in dichloromethane containing silica gel leads to products in which the 2-alkylidene 1,3-dione has been intercepted to give a (most often) crystalline Michael adduct. The yields are usually quite acceptable, especially if the beta-dicarbonyl compound is cyclic. Oxidation of these adducts with sodium periodate regenerates the conjugated enedione, which reacts rapidly with air to give a cyclic peroxide unless protected from the atmosphere. When a monoprotected succinaldehyde is utilized as starting material, hydrolysis of the resultant adduct in aqueous acid results in intramolecular aldolization to give a spirocyclic cyclopentanol.

  DOI：

  10.1021/jo00082a007
• 作为产物：
  描述：

  1,3-环己二酮 、 环己烷基甲醛 在 silica gel 、 苯硫酚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到2-(Cyclohexyl-phenylsulfanyl-methyl)-3-hydroxy-cyclohex-2-enone
  参考文献：
  名称：

  Access to Protected 2-Alkylidene 1,3-diones by Modified Knoevenagel Reaction in the Presence of Thiophenol. A New Approach to Spirocyclopentanol Construction

  摘要：

  A general procedure is described for trapping the products of Knoevenagel condensation involving 1,3-diketones and aliphatic aldehydes. Simple stirring of a three-component mixture consisting of each reactant and thiophenol in dichloromethane containing silica gel leads to products in which the 2-alkylidene 1,3-dione has been intercepted to give a (most often) crystalline Michael adduct. The yields are usually quite acceptable, especially if the beta-dicarbonyl compound is cyclic. Oxidation of these adducts with sodium periodate regenerates the conjugated enedione, which reacts rapidly with air to give a cyclic peroxide unless protected from the atmosphere. When a monoprotected succinaldehyde is utilized as starting material, hydrolysis of the resultant adduct in aqueous acid results in intramolecular aldolization to give a spirocyclic cyclopentanol.

  DOI：

  10.1021/jo00082a007

文献信息

• Fuchs Klaus, Paquette Leo A., J. Org. Chem, 59 (1994) N 3, S 528-532
  作者：Fuchs Klaus, Paquette Leo A.

  DOI：——

  日期：——