(3aS,6aR,8S,9aS,9bS)-8-(1-Hydroxy-1-methyl-ethyl)-octahydro-phenalene-2,5-dione | 159434-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6aR,8S,9aS,9bS)-8-(1-Hydroxy-1-methyl-ethyl)-octahydro-phenalene-2,5-dione
• CAS: 159434-36-3
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: WPZSIBTWVHPZRB-HJSRUMKTSA-N

物化性质

• 沸点：
  422.5±20.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aS,6aR,8S,9aS,9bS)-8-(1-Hydroxy-1-methyl-ethyl)-octahydro-phenalene-2,5-dione 在 吡啶 、 4-二甲氨基吡啶 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 二甲基硫 、 (S)-alpine-hydride 、 sodium methylate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Conformationally Rigid Tricyclic Tripods: Synthesis and Application to Preparation of Enterobactin Analogs

  摘要：

  The syntheses of the conformationally rigid triol 2 and triamine 3 are described. One of the key features of these syntheses was that each of the intermediates involved contained a symmetry element, which made their structure elucidation facile and conclusive. The structural similarity between the platform of enterobactin in its metal binding state and triamine 3 was recognized, and the enterobactin analog 14 was synthesized. The K-f value observed for 14 was as high as the K-f value for enterobactin itself, and higher than the K-f value for any enterobactin analog ever reported. In comparison with a number of synthetic enterobactin analogs, it became evident that the conformational rigidity of the enterobactin platform, resulting in good preorganization of the three catechol moieties toward Fe(III)-chelation, was an important factor contributing to its extraordinarily high K-f.

  DOI：

  10.1021/jo00104a043
• 作为产物：
  描述：

  3,6-Dimethoxynaphthalsaeuredimethylester 在 chromium(VI) oxide 、 乙醇 、 硫酸 、 氨 、 三溴化磷 、 lithium 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 24.0h， 生成 (3aS,6aR,8S,9aS,9bS)-8-(1-Hydroxy-1-methyl-ethyl)-octahydro-phenalene-2,5-dione
  参考文献：
  名称：

  Conformationally Rigid Tricyclic Tripods: Synthesis and Application to Preparation of Enterobactin Analogs

  摘要：

  The syntheses of the conformationally rigid triol 2 and triamine 3 are described. One of the key features of these syntheses was that each of the intermediates involved contained a symmetry element, which made their structure elucidation facile and conclusive. The structural similarity between the platform of enterobactin in its metal binding state and triamine 3 was recognized, and the enterobactin analog 14 was synthesized. The K-f value observed for 14 was as high as the K-f value for enterobactin itself, and higher than the K-f value for any enterobactin analog ever reported. In comparison with a number of synthetic enterobactin analogs, it became evident that the conformational rigidity of the enterobactin platform, resulting in good preorganization of the three catechol moieties toward Fe(III)-chelation, was an important factor contributing to its extraordinarily high K-f.

  DOI：

  10.1021/jo00104a043