2,4-Dihydroxy-benzoic acid (1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl ester | 885218-47-3

• 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: 2,4-Dihydroxy-benzoic acid (1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl ester
• CAS: 885218-47-3
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: SLXDHUHLUNGPPQ-BXWFABGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4-Dihydroxy-benzoic acid (1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl ester 在 chloroamine-T 、 potassium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 14.5h， 生成 [(1S,3aS,7aS)-4,4,7a-trimethyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl] 5-iodo-2,4-bis(oxiran-2-ylmethoxy)benzoate
  参考文献：
  名称：

  Trifunctional norrisolide probes for the study of Golgi vesiculation

  摘要：

  Inspired by the effect of norrisolide on the Golgi complex, we synthesized norrisolide probes that contain: the perhydroindane core of the parent natural product for Golgi localization, a crosslinking unit (aryl azide or epoxide) for covalent binding to the target, and a tag (biotin or iodine) for subsequent target purification. We found that biotin-containing probes 14, 20 and 24 induced inefficient Golgi vesiculation. However, the iodinated probe 25 induced extensive and irreversible Golgi fragmentation. This probe can be used for the isolation of the cellular target of norrisolide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.101
• 作为产物：
  描述：

  2,4-Bis-benzyloxy-benzoic acid (1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以92%的产率得到2,4-Dihydroxy-benzoic acid (1S,3aS,7aS)-4,4,7a-trimethyl-octahydro-inden-1-yl ester
  参考文献：
  名称：

  Chemical Analysis of Norrisolide-Induced Golgi Vesiculation

  摘要：

  The chemical origin of the norrisolide-induced irreversible Golgi vesiculation was studied using a variety of norrisolide probes. This natural product was found to bind to a receptor on the Golgi membranes using the perhydroindane core fragment as the recognition element. The acetylated gamma-lactol-gamma-lactone side chain of norrisolide is essential for the irreversible Golgi vesiculation and can be replaced by other electrophilic motifs without loss of biological function. In particular, compound 10 reproduces the cellular phenotype of the natural product.

  DOI：

  10.1021/ja058259a