(1R,2S,3R,4S)-cyclooctane-1,2,3,4-tetraol | 1254585-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4S)-cyclooctane-1,2,3,4-tetraol
• 英文别名: (1S,2R,3S,4R)-cyclooctane-1,2,3,4-tetrol
• CAS: 1254585-94-8
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: CYTKGVLSBVTIQY-SOSBWXJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R,2R,3R,4S)-cyclooctane-1,2,3,4-tetraacetate 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以98%的产率得到(1R,2S,3R,4S)-cyclooctane-1,2,3,4-tetraol
  参考文献：
  名称：

  含八元环的一些环醇的简洁立体定向合成：环辛烷1,2,3,4-四环

  摘要：

  从顺式，顺式-1，3-环辛二烯开始，简明而有效地合成了环辛烷-1，2，3，4-四环，新的多羟基化的八元碳环。顺式，顺式-1,3-环辛二烯经光氧化制得的环辛烯内过氧化物是合成中的关键化合物。用锌或硫脲还原内过氧化物，然后将羟基乙酰化，将OsO 4 / NMO双键氧化，得到（1 R（S），2 S（R），3 R（S），4 S（R））-环辛烷-1,2,3,4-四醇。有趣的是，环辛烯-1,4-二醇的环氧化米-CPBA也得到反式-环氧二醇17。通过环氧二醇17的水解，容易获得（1R（S），2R（S），3R（S），4S（R））-环辛烷-1,2,3,4-四醇。

  DOI：

  10.1016/j.tet.2010.04.052

文献信息

• Efficient and shortcut syntheses of some novel eight-membered ring cyclitols starting from cycloocta-1,3-diene
  作者：Kadriye Ecer、Emine Salamci

  DOI：10.1016/j.tet.2014.08.060

  日期：2014.11

  Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.