5α-cholesta-7,9(11)-diene-3β,5,6β-triol 3,6-diacetate | 157396-30-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5α-cholesta-7,9(11)-diene-3β,5,6β-triol 3,6-diacetate
• 英文别名: 5-hydroxy-5α-cholesta-7,9(11)-dien-3β,6β-diol 3,6-diacetate；[(3S,5R,6R,10R,13R,14R,17R)-6-acetyloxy-5-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 157396-30-0
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: MPVWWXRKLVQXDR-HLXJSPMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5α-cholesta-7,9(11)-diene-3β,5,6β-triol 3,6-diacetate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以75%的产率得到9α,11α-epoxy-5-hydroxy-5α-cholest-7-en-3β,6β-diol 3,6-diacetate
  参考文献：
  名称：

  CH3ReO3 催化氧化胆甾醇-5,7-二烯-3β-基乙酸酯与尿素-过氧化氢加合物在各种条件下。天然环氧甾醇 9α,11α-epoxy-5α-cholest-7-en-3β,5,6β-triol 的合成

  摘要：

  摘要 本文描述了使用甲基三氧铼 (MTO) 作为催化剂，在各种条件下，用尿素-过氧化氢加合物 (UHP) 氧化 cholesta-5,7-dien-3β-yl acetate (4)。具体而言，研究了使用不同溶剂（CHCl3 和醚）和添加剂（乙醇和吡啶）对 MTO 催化氧化 4 过程的影响。根据化学证据和光谱数据的解释，包括 HH COZY 和 HMBC 实验，从这种氧化中获得的一些新的类固醇（6、9、10 和 11）被分离和表征。MTO/UHP氧化体系氧化4的最佳溶剂是乙醚。在该溶剂中，反应是干净的并且得到作为主要产物的乙酸 5,6β-dihydroxy-5α-cholest-7-en-3β-yl (8, 65% 产率)，以比文献报道的更简单的程序和更高的产率获得。Sterol 8 是合成许多海洋来源的类固醇的关键中间体化合物，具有生物活性，在 B/C 环处氧化。事实上，从二醇 8 开始，我们进行了天然细胞毒性环氧甾醇

  DOI：

  10.1016/s0039-128x(02)00017-x
• 作为产物：
  描述：

  acetoxy-3β hydroxy-5α <*>⁷-cholestenone-6 在 吡啶 、 mercury(II) diacetate 、 borohydride 作用下， 生成 5α-cholesta-7,9(11)-diene-3β,5,6β-triol 3,6-diacetate
  参考文献：
  名称：

  Studies towards the synthesis of polyoxygenated steroids. Reaction of 7,9(11)-diene steroids with RuO4.

  摘要：

  In order to find an entry to C-ring oxygenated steroids, the reaction of ruthenium tetroxide with some Delta(7,9(11))-sterols gas been explored. The reaction has been performed both at -70 degrees C and room temperature using an equimolecular amount of the oxidant and acetone-water as solvent system in the absence of a cooxidant. The change in the temperature conditions moderately affects the yields of the reaction products. When 3 beta,6 alpha- and 3 beta,6 beta-diacetoxy-Delta(7,9(11))-sterols were used the diene system was predominantly attacked at the 9(11)-double bond from the alpha-face of the molecule giving Delta(7)-9 alpha-hydroxy-11-keto- and Delta(7)-9 alpha,11 alpha-dihydroxy-sterols. RuO4 oxidation of cholesta-7,9(11)-dien-3 beta-yl acetate, yielded, in addition to the above oxidation products, minor amounts of three related C-7,C-11 oxigenated 8 alpha,9 alpha-epoxysterols, arising from the oxidation of both double bonds of the diene system. These results, that in part parallel those we recently found on RuO4 oxidation of trisubstituted [Delta(4), Delta(5) and Delta(7)] steroidal alkenes, shed further light on the reactivity of this oxidizing agent which, neverthless, seems far from being completely understood. In addition, our procedure furnishes a reliable route to Delta(7)-9 alpha,11 beta-dihydroxysterols via LiAlH4 reduction of the 11-keto group.

  DOI：

  10.1016/s0040-4020(01)85020-1