3,5-bis(benzyloxy)diazoacetophenone | 52144-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(benzyloxy)diazoacetophenone
• 英文别名: 3,5-Dibenzyloxy-diazo-acetophenone；(2Z)-1-[3,5-bis(phenylmethoxy)phenyl]-2-diazoethanone
• CAS: 52144-91-9
• 化学式: C₂₂H₁₈N₂O₃
• 分子量: 358.397
• InChiKey: WGJQNGJQCNDVLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(benzyloxy)diazoacetophenone 在 氢氧化钾 、 水 、 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 3.67h， 生成 3-(3,5-dibenzyloxybenzoyl)propionic acid
  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：

  3,5-二羟基苯甲酸 在 氢氧化钾 、 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,5-bis(benzyloxy)diazoacetophenone
  参考文献：
  名称：

  在含有间氯-3-羟基酪氨酸的万古霉素生物合成中使用推定的七肽中间体的 (烯丙氧基) 羰基 (Alloc) 化学进行固相合成

  摘要：

  描述了一种在万古霉素生物合成中固相合成假定的线性七肽中间体的简便方法，特别是七肽 D-Leu-Cyt-L-Asn-Hpg-Hpg-Cyt'-Dhpg (Cyt=(2R,3R )-m-chloro-3-hydroxytyrosine, Hpg=(R)-2-(p-hydroxyphenyl)glycine, Cyt'=(2S,3R)-m-chloro-3-hydroxytyrosine and Dhpg=(S)-2- (3,5-二羟基苯基)甘氨酸)。该合成是在氯三苯甲基树脂上进行的，并在肽链组装过程中使用（烯丙氧基）羰基保护基团进行临时 N（α）保护。

  DOI：

  10.1002/1522-2675(20000906)83:9<2572::aid-hlca2572>3.0.co;2-x

文献信息

• A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis
  作者：Shinichiro Fuse、Yuma Otake、Yuto Mifune、Hiroshi Tanaka

  DOI：10.1071/ch15342

  日期：——

  An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl

  演示了高效的单流Arndt-Eistert合成。在微流系统中进行了一系列酰氯形成过程–亲核酰基取代–沃尔夫重排–亲核加成反应，而没有分离出包括可能具有爆炸性的化合物在内的任何中间体。微流系统由简单，便宜且易于获得的仪器和管制成。分别以33％和23％的产率（三个步骤）制备α-芳基酯2a和2b。
• Synthesis of bikaverin
  作者：Nobuya Katagiri、Jun Nakano、Tetsuzo Kato

  DOI：10.1039/p19810002710

  日期：——
• US3937838A
  申请人：——

  公开号：US3937838A

  公开（公告）日：1976-02-10
• US4011258A
  申请人：——

  公开号：US4011258A

  公开（公告）日：1977-03-08
• A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4′′-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium
  作者：Maria Szirmai、Helena Odqvist、Magnus M. Halldin

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

  日期：1996.4

  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.