5β-pregnan-3α-ol | 4352-07-2

• 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
• 英文名称: 5β-pregnan-3α-ol
• 英文别名: 5β-pregnanol-(3α)；(10S)-3t-Hydroxy-10r.13c-dimethyl-17c-aethyl-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3α-Hydroxy-10.13-dimethyl-17β-aethyl-5β-gonan；(3R,5R,8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 4352-07-2
• 化学式: C₂₁H₃₆O
• 分子量: 304.516
• InChiKey: CEBZORSAHLSRQW-MLNSIODZSA-N

物化性质

• 沸点：
  394.7±10.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5β-pregnan-3α-ol 在 pyridinium chlorochromate 作用下， 生成 5β-pregnan-3-one
  参考文献：
  名称：

  Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis

  摘要：

  Mild and regioselective conversion of 3-keto-5 alpha- and 3-keto-5 beta-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Delta(1)- and Delta(4)-3-ketones) by treatment with oiodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the alpha- and beta-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.11.007
• 作为产物：
  描述：

  孕烷醇酮 在 盐酸 、 amalgamated zinc 、 溶剂黄146 作用下， 生成 5β-pregnan-3α-ol
  参考文献：
  名称：

  Sterols. XLIV. Pregnanone-3 and Related Compounds^*

  摘要：

  DOI：

  10.1021/ja01277a040

文献信息

• A New Class of Potent <i>N</i>-Methyl-<scp>d</scp>-Aspartate Receptor Inhibitors: Sulfated Neuroactive Steroids with Lipophilic D-Ring Modifications
  作者：Eva Kudova、Hana Chodounska、Barbora Slavikova、Milos Budesinsky、Michaela Nekardova、Vojtech Vyklicky、Barbora Krausova、Pavel Svehla、Ladislav Vyklicky

  DOI：10.1021/acs.jmedchem.5b00570

  日期：2015.8.13

  promising therapeutic targets. In this study, we describe a new class of neurosteroid analogues which possess structural modifications in the steroid D-ring region. These analogues were tested on recombinant GluN1/GluN2B receptors to evaluate the structure–activity relationship. Our results demonstrate that there is a strong correlation between this new structural feature and the in vitro activity, as all

  Ñ -甲基- d天门冬氨酸受体（NMDARs）是谷氨酸门控离子通道，在兴奋性突触传递中起关键作用。但是，NMDAR的过度激活可能导致兴奋性毒性细胞损伤/死亡，因此，它们在许多神经病理学疾病中发挥作用。已知NMDAR的活性受多种变构调节剂（包括神经甾体）的影响，这反过来又使它们成为有希望的治疗靶标。在这项研究中，我们描述了一类新的类固醇神经类似物，在类固醇D环区域具有结构修饰。这些类似物在重组GluN1 / GluN2B受体上进行了测试，以评估其结构与活性之间的关系。我们的结果表明，这种新的结构特征与体外活性之间存在很强的相关性，与已知的内源性神经甾体-孕烯醇酮硫酸盐（IC 50 = 24.6μM）相比，有50个值在90 nM至5.4μM之间变化。
• Sterols. LI. Δ⁴-Pregnenone-3
  作者：Russell E. Marker、Elmer J. Lawson

  DOI：10.1021/ja01872a014

  日期：1939.3
• Method for the preparation of steroidal carbinols
  申请人：PARKE DAVIS &

  公开号：US02306635A1

  公开（公告）日：1942-12-29
• Pierce et al., Journal of the Chemical Society, 1955, p. 694,701
  作者：Pierce et al.

  DOI：——

  日期：——
• Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis
  作者：Takashi Iida、Kaoru Omura、Ryou Sakiyama、Mitsuo Kodomari

  DOI：10.1016/j.chemphyslip.2013.11.007

  日期：2014.2

  Mild and regioselective conversion of 3-keto-5 alpha- and 3-keto-5 beta-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Delta(1)- and Delta(4)-3-ketones) by treatment with oiodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the alpha- and beta-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones. (C) 2013 Elsevier Ireland Ltd. All rights reserved.