3,5-Dibenzyloxyphenacylmalonsaeure | 71186-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-Dibenzyloxyphenacylmalonsaeure
• CAS: 71186-03-3
• 化学式: C₂₅H₂₂O₇
• 分子量: 434.445
• InChiKey: MCGURGANVTXINO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  110.13
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,5-Dibenzyloxyphenacylmalonsaeure 在 palladium dihydroxide 甲烷磺酸 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 35.5h， 生成
  参考文献：
  名称：

  A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4′′-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium

  摘要：

  The first synthesis of 4 ''-hydroxyd-Delta(1)-THC-7-oic acid, one of the three major metabolites of dl-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydroxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4 ''-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBH4 afforded the secondary alcohol in the side-chain. Acetylation and removal of the 13-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using NaClO2 followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4 ''-hydroxy-Delta(1)-THC-7-oic acid.

  DOI：

  10.1002/(sici)1099-1344(199604)38:4<309::aid-jlcr775>3.0.co;2-5
• 作为产物：
  描述：

  3,5-dibenzyloxylbenzoyl chloride 在 氢氧化钾 、 水 、 氢溴酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 5.17h， 生成 3,5-Dibenzyloxyphenacylmalonsaeure
  参考文献：
  名称：

  A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4′′-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium

  摘要：

  The first synthesis of 4 ''-hydroxyd-Delta(1)-THC-7-oic acid, one of the three major metabolites of dl-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydroxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4 ''-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBH4 afforded the secondary alcohol in the side-chain. Acetylation and removal of the 13-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using NaClO2 followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4 ''-hydroxy-Delta(1)-THC-7-oic acid.

  DOI：

  10.1002/(sici)1099-1344(199604)38:4<309::aid-jlcr775>3.0.co;2-5