双醋酸脱氢皮质醇 | 98523-85-4

• 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
• 中文名称: 双醋酸脱氢皮质醇
• 中文别名: 醋酸泼尼松龙EP杂质C；双醋酸泼尼松龙
• 英文名称: prednisolone 11β,21-diacetate
• 英文别名: 11β,21-diacetoxy-17-hydroxy-pregna-1,4-diene-3,20-dione；11β,21-Diacetoxy-17-hydroxy-pregna-1,4-dien-3,20-dion；Prednisolone 11,21-Diacetate；[2-[(8S,9S,10R,11S,13S,14S,17R)-11-acetyloxy-17-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 98523-85-4
• 化学式: C₂₅H₃₂O₇
• 分子量: 444.525
• InChiKey: NTDDKQGHIJOKSN-WEXULQILSA-N

物化性质

• 熔点：
  227-229 °C
• 沸点：
  582.0±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  双醋酸脱氢皮质醇 在 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以91%的产率得到泼尼松龙
  参考文献：
  名称：

  Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

  摘要：

  Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3 beta-O-acetyl group in the presence of the 6 beta group in 3 beta,6 beta-Di-O-acetyl-5 alpha-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3 beta, 5 alpha, 6 beta-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.004
• 作为产物：
  描述：

  11β,21-diacetoxy-9-chloro-17-hydroxy-pregna-1,4-diene-3,20-dione 在 过氧化氢异丙苯 作用下， 以 1,4-二氧六环 为溶剂， 以93%的产率得到双醋酸脱氢皮质醇
  参考文献：
  名称：

  一种9-卤代甾体激素化合物9-位脱卤的制备 方法

  摘要：

  本发明公开了一种甾体激素化合物9‑位脱卤的方法，该方法步骤：将9‑卤代‑11‑羟基甾体化合物或者9‑卤代‑11‑羟基酯甾体化合物溶于有机溶剂中，升温至一定温度后，缓慢加入适量的脱卤试剂，反应一段时间后检测，待反应完全，减压浓缩除去部分溶剂，降温析晶或者加水析晶，析出固体，过滤得到目标产物11‑羰基甾体化合物或者11‑羟基酯甾体化合物。本发明操作简单，反应杂质少，收率高，同时避免了金属脱卤剂和巯基脂肪酸的使用，减少了三废污染，适用于工业化生产。

  公开号：

  CN111333690B

文献信息

• Effective High-Pressure Cleavage of Sterically Hindered Steroid Esters
  作者：Wojciech Kroszczyński、Ewa Olszewska、Piotr Sałański、Janusz Jurczak

  DOI：10.1002/hlca.200490135

  日期：2004.6

  A simple and effective method to deprotect of sterically hindered steroid esters is described. Deprotection was carried out in MeOH in the presence of a catalytic amount of Et3N under high-pressure conditions. Enzymatic, anionite, and high-pressure methods are compared.

  描述了一种简单有效的方法来保护位阻类固醇酯的保护。在高压条件下，在催化量的Et 3 N存在下，在MeOH中进行脱保护。比较了酶法，阴离子法和高压法。
• Simple procedure for reductive coupling of steroids with a cross conjugated dienone system
  作者：A. Schmidt、R. Beckert、D. Weiß

  DOI：10.1016/s0040-4039(00)74243-2

  日期：1992.7

  A simple procedure was found to dimerize cross conjugated dienones to the corresponding olefins. In contrast to the McMurry reaction this variant works without titanium halides. Bis-steroids which may be of pharmacological importance are prepared in high yields.

  发现一种简单的方法将交叉共轭二烯酮二聚为相应的烯烃。与McMurry反应相反，该变体无需卤化钛即可使用。以高收率制备可能具有药理学重要性的双甾族化合物。
• TW2016/9789
  申请人：——

  公开号：——

  公开（公告）日：——
• USZYCKA-HORAWA, T.;KROSZCZYNSKI, W., BOLL. CHIM. FARM., 129,(1990) N, C. 230-232
  作者：USZYCKA-HORAWA, T.、KROSZCZYNSKI, W.

  DOI：——

  日期：——
• Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
  作者：Shao-Min Wang、Yan-Bing Zhang、Hong-Min Liu、Guo-Bin Yu、Ke-Rang Wang

  DOI：10.1016/j.steroids.2006.10.004

  日期：2007.1

  Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3 beta-O-acetyl group in the presence of the 6 beta group in 3 beta,6 beta-Di-O-acetyl-5 alpha-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3 beta, 5 alpha, 6 beta-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species. (c) 2006 Elsevier Inc. All rights reserved.