3-hydroxy-6,7,9,11-tetramethyl-2-(phenylsulfonyl)cyclopentaheptalene-1(1H)-one

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-hydroxy-6,7,9,11-tetramethyl-2-(phenylsulfonyl)cyclopentaheptalene-1(1H)-one
• 英文别名: 4-(Benzenesulfonyl)-5-hydroxy-9,11,13,15-tetramethyltricyclo[8.5.0.02,6]pentadeca-1,4,6,8,10,12,14-heptaen-3-one
• 化学式: C₂₅H₂₂O₄S
• 分子量: 418.513
• InChiKey: ZHQRHKKCYXBVDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl 5,6,8,10-tetramethylheptalene-1,2-dicarboxylate 在 正丁基锂 、 (benzenesulfonyl)methyllithium 作用下， 以 四氢呋喃 为溶剂， 反应 74.0h， 生成 3-hydroxy-6,7,9,11-tetramethyl-2-(phenylsulfonyl)cyclopentaheptalene-1(1H)-one
  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).