3-<(4-methoxyphenyl)sulfonyl>-7,8,10,12-tetramethylbenzoheptalene-2,4-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<(4-methoxyphenyl)sulfonyl>-7,8,10,12-tetramethylbenzoheptalene-2,4-diol
• 英文别名: 3-(4-methoxyphenyl)sulfonyl-7,8,10,12-tetramethylbenzo[a]heptalene-2,4-diol
• 化学式: C₂₇H₂₆O₅S
• 分子量: 462.566
• InChiKey: DPOOFKJJMBMURX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-甲氧基茴香硫醚 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 反应 17.5h， 生成 3-<(4-methoxyphenyl)sulfonyl>-7,8,10,12-tetramethylbenzoheptalene-2,4-diol
  参考文献：
  名称：

  Formation of 3-Sulfonyl-Substituted Benzo[a]heptalene-2,4-diols from Heptalene-1,2-dicarboxylates and Lithiomethyl Phenyl Sulfones

  摘要：

  On treatment with 6 mol-equiv, of lithiomethyl phenyl sulfone at -78 degrees in THF, dimethyl 5,6,8,10-tetramethylhrptalene-1,2w-dicarboxylate (1b) gives, after raising the temperature to -10 degrees and addition of 6 mol-equiv. of BuLi; followed by further warming to ambient temperature, the corresponding 3-(phenyl- sulfonyl)benzo[a]haptalene-2,4-diol 2b in yields up to 65% (cf. Scheme 6 and Table 2),in contrast to its double-bond-shifted (DBS) isomer Ib which gave 2b in a yield of only 6% [1]. The bisanion [9](2-) of the cyclopenta[a]heptalen-1(1H)-one9 (cf. Fig. I),carrying a (phenylsulfonyl)methyl substituent at C(11b), seems to be a key intermediate on the reaction path to 2b, because 9 is transformed in high yield into 2b in the presence of 6 mol-equiv. of BuLi in the temperature range of -10 degrees to room temperature (cf Scheme 7). Heptalene-dicarboxylate 1'b was also transformed into benzo[a]heptalene-2,4-diols 2c-g by a number of lithiated methyl X-phenyl sulfones and BuLi (cf. Scheme 9 and Table 3).

  DOI：

  10.1002/(sici)1522-2675(19990310)82:3<372::aid-hlca372>3.0.co;2-h

文献信息

• Formation of 3-Sulfonyl-Substituted Benzo[a]heptalene-2,4-diols from Heptalene-1,2-dicarboxylates and Lithiomethyl Phenyl Sulfones
  作者：Marc Lutz、Anthony Linden、Khaled Abou-Hadeed、Hans-Jürgen Hansen

  DOI：10.1002/(sici)1522-2675(19990310)82:3<372::aid-hlca372>3.0.co;2-h

  日期：1999.3.10

  On treatment with 6 mol-equiv, of lithiomethyl phenyl sulfone at -78 degrees in THF, dimethyl 5,6,8,10-tetramethylhrptalene-1,2w-dicarboxylate (1b) gives, after raising the temperature to -10 degrees and addition of 6 mol-equiv. of BuLi; followed by further warming to ambient temperature, the corresponding 3-(phenyl- sulfonyl)benzo[a]haptalene-2,4-diol 2b in yields up to 65% (cf. Scheme 6 and Table 2),in contrast to its double-bond-shifted (DBS) isomer Ib which gave 2b in a yield of only 6% [1]. The bisanion [9](2-) of the cyclopenta[a]heptalen-1(1H)-one9 (cf. Fig. I),carrying a (phenylsulfonyl)methyl substituent at C(11b), seems to be a key intermediate on the reaction path to 2b, because 9 is transformed in high yield into 2b in the presence of 6 mol-equiv. of BuLi in the temperature range of -10 degrees to room temperature (cf Scheme 7). Heptalene-dicarboxylate 1'b was also transformed into benzo[a]heptalene-2,4-diols 2c-g by a number of lithiated methyl X-phenyl sulfones and BuLi (cf. Scheme 9 and Table 3).