dimethyl 5-methoxy-19-oxotetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-hexaene-1,10-dicarboxylate | 425365-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 5-methoxy-19-oxotetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-hexaene-1,10-dicarboxylate
• CAS: 425365-16-8
• 化学式: C₂₄H₂₄O₆
• 分子量: 408.451
• InChiKey: GLTMCMOLNCNWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl 5-methoxy-19-oxotetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-hexaene-1,10-dicarboxylate 在 氢氧化钾 、 氢溴酸 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 5-Hydroxytetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-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
• 作为产物：
  描述：

  1,2-二(溴甲基)苯 在 sodium hydroxide 、 四丁基溴化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 dimethyl 5-methoxy-19-oxotetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-hexaene-1,10-dicarboxylate
  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