(20R)-5beta-孕甾烷-3alpha,17,20-三醇 | 1165-28-2

• 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: (20R)-5beta-孕甾烷-3alpha,17,20-三醇
• 中文别名: 5β-孕烷-3α,17α,20β-三醇
• 英文名称: 3α,17α,20α-trihydroxy-5β-pregnane
• 英文别名: 5β-pregnane-3α,17α,20α-triol；5β-pregnan-3α,17α,20α-triol；5β-pregnane-3α,17,20β_F-triol；5β-Pregnan-3α,17,20β_F-triol；(10S)-3t.17t-Dihydroxy-10r.13c-dimethyl-17c-((R)-1-hydroxy-aethyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3α.17α-Dihydroxy-10.13-dimethyl-17β-((R)-1-hydroxy-aethyl)-5β-gonan；(20R)-5beta-Pregnane-3alpha,17,20-triol；(3R,5R,8R,9S,10S,13S,14S,17R)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 1165-28-2
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: SCPADBBISMMJAW-OYMMSLOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20R)-5beta-孕甾烷-3alpha,17,20-三醇 在 甲醇 、 过碘酸 作用下， 生成 还原胆烷醇酮
  参考文献：
  名称：

  Preschoolers' Inhibition in Their Home: Relation to Temperament

  摘要：

  Researchers assessed 58 preschoolers' reactions to an unfamiliar person and unfamiliar objects in their familiar home environment. Children participated in a 30-min procedure designed to elicit behavioral inhibition, including (a) a free-play period with a stranger present, (b) a structured interaction with the stranger, and (c) uncertainty-eliciting tasks, Behaviors representing the child's reactions toward the mother, stranger, and novel objects were coded, Mothers completed a temperament scale. Preschoolers exhibited behaviors indicative of inhibition toward unfamiliar social and nonsocial stimuli; behaviors remained stable across increasingly intrusive episodes. The approach/withdrawal component of temperament was related to behavioral inhibition. Individual differences in mood did not appear to be related to differences in inhibition. Parent reported temperament was related to researcher-observed behaviors.

  DOI：

  10.1080/00221320209598688
• 作为产物：
  描述：

  (5S,8R,9S,10S,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,4,5,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 生成 (20R)-5beta-孕甾烷-3alpha,17,20-三醇
  参考文献：
  名称：

  5β-Pregn-6-ene-3α，17,20-三醇

  摘要：

  已经制备了5β-Pregn-6-ene-3α，17,20α-三醇（I）及其20β-异构体（II），并用氢还原成相应的孕烷。

  DOI：

  10.1039/p19760000452

文献信息

• Diethylhydrogensilyl cyclic diethylsilylene derivatives in gas chromatography-mass spectrometry of hydroxylated steroids. II. Pregnanes with a hydroxylated 17.BETA.-side-chain.
  作者：MASATAKA ISHIBASHI、MASAHIRO ITOH、KOUWA YAMASHITA、HIROSHI MIYAZAKI、HISAO NAKATA

  DOI：10.1248/cpb.34.3298

  日期：——

  The gas chromatographic-mass spectrometric properties of diethylhydrogensilyl cyclic diethylsilylene derivatives of hydroxypregnanes were studied. Pregnanes with a sterically hindered 11β-hydroxyl group were smoothly silylated with a new silylating agent, N, O-bis(diethylhydrogensilyl)-trifluoroacetamide, under mild conditions. The mass spectra of these derivatives were characterized by the appearance of the intense molecular ion peak, which provides convenient and reliable confirmation of the molecular weight of these hydroxypregnanes. The most characteristic fragment ions were those at m/z 185 for 17, 20-diols and at m/z 287 for 17, 20, 21-triols, which were produced by cleavage at the C(13)-C(17) and C(15)-C(16) bonds with hydrogen atom transfer. This indicates that all of the major fragmentations are directed by the cyclic diethylsilylene group. Another fragmentation common to the spectra was the successive loss of diethylhydrogensilanol from the molecular ion. A remarkable difference in the appearance of peaks was observed between DEHS-DES derivatives of a 17α, 20α, 21-triol and its 20β-isomer. Structures are proposed for some of these fragment ions.

  研究了羟基孕烷的二乙基氢硅烷基环二乙基硅烷衍生物的气相色谱-质谱特性。在温和的条件下，用一种新的硅烷化剂 N, O-双（二乙基氢代苯甲酰）-三氟乙酰胺顺利地硅烷化了带有立体受阻的 11β- 羟基的孕烷。这些衍生物的质谱特征是出现了强烈的分子离子峰，这为确定这些羟基孕烷的分子量提供了方便可靠的依据。最有特征的碎片离子是 17、20-二醇的 m/z 185 和 17、20、21-三醇的 m/z 287，它们是通过氢原子转移裂解 C(13)-C(17) 和 C(15)-C(16) 键产生的。这表明所有主要碎片都是由环状二乙基硅基引导的。光谱中的另一个共同碎片是分子离子中的二乙基氢硅醇相继消失。在 17α、20α、21-三醇的 DEHS-DES 衍生物与其 20β 异构体之间，观察到峰值出现的明显差异。提出了其中一些碎片离子的结构。
• Synthesis of the four pairs of side-chain epoxides epimeric at C-20 derived from 5.beta.-pregnan-3.alpha.-ol
  作者：Marvin L. Lewbart

  DOI：10.1021/jo01269a001

  日期：1968.5
• Synthesis of 17α,20α-Dihydroxysteroids¹
  作者：DAVID K. FUKUSHIMA、EVELYN D. MEYER

  DOI：10.1021/jo01096a006

  日期：1958.2
• De Courcy; Schneider, Chemistry and industry, 1956, p. 315
  作者：De Courcy、Schneider

  DOI：——

  日期：——
• De Courcy; Schneider, Journal of Biological Chemistry, 1956, vol. 223, p. 865,871
  作者：De Courcy、Schneider

  DOI：——

  日期：——