3-Hydroxy-2-[phenylsulfanyl(15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methyl]cyclohex-2-en-1-one | 154876-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Hydroxy-2-[phenylsulfanyl(15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methyl]cyclohex-2-en-1-one
• CAS: 154876-46-7
• 化学式: C₂₉H₂₆O₂S
• 分子量: 438.59
• InChiKey: UXFUODISDMCESE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  3-Hydroxy-2-[phenylsulfanyl(15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methyl]cyclohex-2-en-1-one 在 sodium periodate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.0h， 生成 8a-hydroxyspiro[7,8-dihydro-6H-1,2-benzodioxine-3,15'-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene]-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：

  9,10-dihydro-9,10-ethanoanthracene-11-carbaldehyde 、 1,3-环己二酮 在 silica gel 、 苯硫酚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到3-Hydroxy-2-[phenylsulfanyl(15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)methyl]cyclohex-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

• 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：——
• 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.