5-Hydroxy-6-methylsulfanyltetracyclo[8.8.1.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaen-19-one | 425365-20-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-Hydroxy-6-methylsulfanyltetracyclo[8.8.1.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaen-19-one
• CAS: 425365-20-4
• 化学式: C₂₀H₂₀O₂S
• 分子量: 324.444
• InChiKey: AADLEZLIDIYMGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  乙二醇 、 5-Hydroxy-6-methylsulfanyltetracyclo[8.8.1.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaen-19-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到6'-Methylsulfanylspiro[1,3-dioxolane-2,19'-tetracyclo[8.8.1.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaene]-5'-ol
  参考文献：
  名称：

  Syntheses of new hydroxy-[3.3]orthocyclophanes as models for the galactose oxidase Tyr-Cys cofactor

  摘要：

  The syntheses of 3,4-benzo-8,9-(3'-hydroxybenzo)bicyclo[4,4,1]undeca-3,8-dien-11-one, 3,4-benzo-8,9-(3'-hydroxy-4'-methyl-sulfanylbenzo)bicyclo[4,4,1]undeca-3,8-dien-11-one and their ethylene acetals have been achieved. Crystallographic, UV/Vis and NMR data show that the two ketones adopt boat/chair conformations that are fluxional in solution, while the acetals exhibit chair/chair conformations with layered benzo rings. Comparison of the oxidation potentials of the four compounds suggests that an ortho-methylsulfanyl substituent and a pi-pi interaction both thermodynamically stabilise the phenoxonium radical species derived from these compounds, by approximately equal amounts. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01175-9
• 作为产物：
  描述：

  3,4-(4-methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,9-dien-11-one 在 氢溴酸 、 对甲苯磺酸 作用下， 反应 75.0h， 生成 5-Hydroxy-6-methylsulfanyltetracyclo[8.8.1.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaen-19-one
  参考文献：
  名称：

  Syntheses of new hydroxy-[3.3]orthocyclophanes as models for the galactose oxidase Tyr-Cys cofactor

  摘要：

  The syntheses of 3,4-benzo-8,9-(3'-hydroxybenzo)bicyclo[4,4,1]undeca-3,8-dien-11-one, 3,4-benzo-8,9-(3'-hydroxy-4'-methyl-sulfanylbenzo)bicyclo[4,4,1]undeca-3,8-dien-11-one and their ethylene acetals have been achieved. Crystallographic, UV/Vis and NMR data show that the two ketones adopt boat/chair conformations that are fluxional in solution, while the acetals exhibit chair/chair conformations with layered benzo rings. Comparison of the oxidation potentials of the four compounds suggests that an ortho-methylsulfanyl substituent and a pi-pi interaction both thermodynamically stabilise the phenoxonium radical species derived from these compounds, by approximately equal amounts. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01175-9