11β,18,21-trihydroxy-4-pregnen-3,20-dione | 3885-55-0

• 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: 11β,18,21-trihydroxy-4-pregnen-3,20-dione
• 英文别名: 18-hydroxycorticosterone；(1S,2S,5S,9R,11S,12S,13R)-6,11-dihydroxy-6-(hydroxymethyl)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-17-en-16-one
• CAS: 3885-55-0
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: AVWPDLYUUUBBBW-OQNMBHLBSA-N

物化性质

• 沸点：
  586.8±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-孕烯-3,11,20-三酮 在 lead(IV) acetate 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 氢氧化钾 、 lithium aluminium tetrahydride 、 水 、 碘 、 silver(I) acetate 、 乙酸酐 、 铬酸 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 35.92h， 生成 11β,18,21-trihydroxy-4-pregnen-3,20-dione
  参考文献：
  名称：

  18取代的类固醇。第8部分。改进的11β，18,21-三羟基pregn-4-ene-3,20-二酮（'18-羟基皮质酮'）的合成

  摘要：

  通过应用“次碘酸盐”系列反应[Pb（OAc）4 –I 2 – hν ; 氧化 溶剂化]，然后在乙酸中的乙酸四乙酸铅在C-21处进行乙酰氧基化。然后碱性水解得到18-羟基皮质酮。

  DOI：

  10.1039/p19810000703

文献信息

• A convenient synthesis of 18-hydroxycorticosterone and 18-hydroxy-11-desoxycorticosterone via stereospecific hypoiodination of 20-hydroxysteroids
  作者：Ahmed Boudi、Pascale Lemoine、Bernard Viossat、Alain Tomas、Jean Fiet、Hervé Galons

  DOI：10.1016/s0040-4020(99)00187-8

  日期：1999.4

  18-Hydroxycorticosterone and 18-hydroxy-11-desoxycorticosterone, were obtained via hypoiodination of 20-hydroxy derivatives. The absolute configurations of the C-20 were established by X-ray, only the 20S alcohols reacted under the hypoiodination conditions.

  通过20-羟基衍生物的亚碘化获得18-羟基皮质酮和18-羟基-11-脱氧皮质酮。C-20的绝对构型通过X射线确定，只有20S醇在低碘化条件下反应。
• Differences between adrenal adenoma causing primary aldosteronism and other adrenal tissues in the incorporation of labeled steroid precursors into their products
  作者：Toshitaka Usa、Arunabha Ganguly、Myron H. Weinberger

  DOI：10.1016/0039-128x(80)90076-8

  日期：1980.11

  The incorporation and conversion of several labeled steroid precursors into their products were examined in slices of adrenal tissue from two patients with primary aldosteronism and compared with that in "normal" adrenal tissue and adrenal tissues from a patient with Cushing's syndrome. The products of the incorporation were separated by Sephadex LH-20 column chromatography. The major products of conversion in the adenomatous tissue of primary aldosteronism were 18-hydroxycorticosterone and lesser amounts of aldosterone. Smaller amounts of 18-hydroxycorticosterone were isolated from all other adrenal tissues studied. No aldosterone could be recovered after incubating any of the adrenal tissue studied with labeled 18-hydroxy-11-deoxycorticosterone or 18-hydroxycorticosterone as precursor steroid. These in vitro results seem to suggest that there is increased 18-hydroxylation in the adenoma of primary aldosteronism compared with other tissues and that relatively more 18-hydroxycorticosterone is produced in such tissue than aldosterone.
• Kirk, David N.; Slade, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2591 - 2596
  作者：Kirk, David N.、Slade, Christopher J.

  DOI：——

  日期：——