(3a'S,4'R,5'R,6a'R)-5'-hydroxy-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde | 1374991-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3a'S,4'R,5'R,6a'R)-5'-hydroxy-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde
• 英文别名: (1'R,2'R,3'aR,6'aS)-2'-hydroxy-5,5-dimethylspiro[1,3-dioxane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-1'-carbaldehyde
• CAS: 1374991-61-3
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: PJVZHZBKZPUPAW-WRWGMCAJSA-N

物化性质

• 沸点：
  382.9±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3a'S,4'R,5'R,6a'R)-5'-hydroxy-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde 、 5-[(2S,3S)-2-(methoxymethoxy)-3-methylhept-5-ynyl]sulfonyl-1-phenyltetrazole 在 盐酸 、 六甲基磷酰三胺 、 水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 26.83h， 生成 (+)-(3aS,4R,5R,6aR)-5-hydroxy-4-((3S,4S,E)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)hexahydropentalene-2(1H)-one
  参考文献：
  名称：

  A carbohydrate approach for the formal total synthesis of the prostacyclin analogue (16S)-iloprost

  摘要：

  The formal total synthesis of the synthetic and stable analogue of prostacyclin, (16S)- iloprost is described via a convergent synthesis starting from readily available D-glucose. Julia olefination and the aldol reaction are the key steps involved in the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.005
• 作为产物：
  描述：

  ((3a'S,4'R,5'R,6a'R)-5'-hydroxy-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-yl)ethane-1,2-diol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以96%的产率得到(3a'S,4'R,5'R,6a'R)-5'-hydroxy-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde
  参考文献：
  名称：

  A carbohydrate approach for the formal total synthesis of the prostacyclin analogue (16S)-iloprost

  摘要：

  The formal total synthesis of the synthetic and stable analogue of prostacyclin, (16S)- iloprost is described via a convergent synthesis starting from readily available D-glucose. Julia olefination and the aldol reaction are the key steps involved in the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.005

文献信息

• PROSTACYCLIN DERIVATIVES
  申请人：Tung Roger

  公开号：US20100184862A1

  公开（公告）日：2010-07-22

  This invention relates to novel prostacyclin derivatives, their acceptable acid addition salts, solvates, hydrates and polymorphs thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by prostacyclin, and in particular those diseases and conditions beneficially treated by dilators of systemic and pulmonary arterial vascular beds or by platelet aggregation inhibitors.

  本发明涉及新型前列环素衍生物及其可接受的酸加盐、溶剂、水合物和多晶形态。本发明还提供了包含本发明化合物的组合物，并且提供了使用这些组合物治疗疾病和状况的方法，这些疾病和状况通过扩张系统和肺动脉血管床或通过血小板聚集抑制剂得到有益治疗。