2-[3-(1,3-Dioxan-2-yl)-1-phenylsulfanylpropyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one | 154876-43-4

• 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-[3-(1,3-Dioxan-2-yl)-1-phenylsulfanylpropyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
• CAS: 154876-43-4
• 化学式: C₂₁H₂₈O₄S
• 分子量: 376.517
• InChiKey: FZIBFVXNSPNZSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(1,3-Dioxan-2-yl)-1-phenylsulfanylpropyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 4-(2-Hydroxy-4,4-dimethyl-6-oxo-cyclohex-1-enyl)-4-phenylsulfanyl-butyraldehyde 、 1-Hydroxy-8,8-dimethyl-4-phenylsulfanyl-spiro[4.5]decane-6,10-dione
  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：

  2-(2-溴乙基)-1,3-二氧杂环己烷 在 silica gel 、 magnesium 、 苯硫酚 、 1,2-二溴乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 2-[3-(1,3-Dioxan-2-yl)-1-phenylsulfanylpropyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-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

文献信息

• Access to Protected 2-Alkylidene 1,3-diones by Modified Knoevenagel Reaction in the Presence of Thiophenol. A New Approach to Spirocyclopentanol Construction
  作者：Klaus Fuchs、Leo A. Paquette

  DOI：10.1021/jo00082a007

  日期：1994.2

  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.