3,4-(4-methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,9-dien-11-one | 425365-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3,4-(4-methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,9-dien-11-one
• 英文别名: 5-Methoxytetracyclo[8.8.1.03,8.012,17]nonadeca-3(8),4,6,12,14,16-hexaen-19-one
• CAS: 425365-18-0
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: PUXNMAHTMZBVCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-(4-methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,9-dien-11-one 在 氢溴酸 作用下， 反应 3.0h， 以73%的产率得到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：

  dimethyl 1,2,4,5-tetrahydro-3-oxobenzocycloheptene-2,4-dicarboxylate 在 氢氧化钾 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 3,4-(4-methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,9-dien-11-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

文献信息

• 3,4-(4-Methoxybenzo):8,9-benzobicyclo[4.4.1]undeca-3,8-dien-11-one ethylene acetal
  作者：Xiaoming Liu、Colin A. Kilner、Malcolm A. Halcrow

  DOI：10.1107/s0108270102001816

  日期：2002.4.15

  The title compound, 5-methoxyspiro[tetracyclo[8.8.1.0(3,8).0 (12,17)]nonadeca-3,5,7,12,14,16-hexene-19,2'-[1,3]dioxolane], C22H24O3, exhibits a twin-chair conformation with the aromatic rings overlying each other. Comparison of the dihedral angle between these two rings with those from previously reported [3.3]orthocyclophanes of this type suggests the presence of a weak attractive charge-transfer interaction between the two, different, stacked arenes.