(20S)-20-hydroxy-5β-pregnan-3α-yl acetate | 6100-25-0

• 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: (20S)-20-hydroxy-5β-pregnan-3α-yl acetate
• 英文别名: (2S)-20-hydroxy-5β-pregnan-3α-yl acetate；pregnanediol 3-monoacetate；3α-acetoxy-5β-pregnan-20α_F-ol；(10S)-3t-Acetoxy-10r.13c-dimethyl-17c-((S)-1-hydroxy-aethyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-(20α_F-hydroxy-5β-pregnanyl-(3α)-ester)；3α-Acetoxy-5β-pregnan-20α(F)-ol；Pregnane-3,20-diol, 3-acetate, (3I+/-,5I(2),20S)-；[(3R,5R,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 6100-25-0
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: RDRFJIOUMNDZPW-KWTODDMMSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  448.4±18.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20S)-20-hydroxy-5β-pregnan-3α-yl acetate 以 吡啶 为溶剂， 反应 4.0h， 生成 3α-acetoxy-5β-pregn-17(20)-ene
  参考文献：
  名称：

  Isolation and structural elucidation of the degradation products of pregnanediol disulfate obtained by hot acid hydrolysis (Clinical analysis on steroids. XXI).

  摘要：

  除了主要产品17α-乙基-17β-甲基-18-去氢-5β-雄甾-13-烯-3α-醇（7a）、17α-甲基-D-同雄甾-5β-醇（8）和17α-甲基-17β-氯-D-同雄甾-5β-醇（9），在3 N盐酸回流条件下还获得了孕醇-3,20-二硫酸酯（2）的其他少量降解产物，并通过与合成样品的比较对其结构进行了鉴定。分离得到的类固醇单烯包括5β-孕-3-烯-20α-醇（10a）、5β-孕-2-烯-20α-醇（11a）、5β-孕-20-烯-3α-醇（12a）和5β-孕-17（20）-烯-3α-醇（13a）。以气相色谱法检测到的13a的Z异构体为5β-孕-17（20）-烯-3α-醇（14a），并通过与合成化合物的气相色谱-质谱比较进行了鉴定。分离的类固醇二烯作为混合物包括具有部分D环结构的Δ2和Δ3化合物，对应于7a、12a和13a。虽然它是一个少量产物，5β-孕烷-3α、20β-二醇（16）也被获得，其分离表明在水解过程中形成了C20碳正离子。完整类固醇孕醇（1）的产率仅为获得的总产品的18.4%。

  DOI：

  10.1248/cpb.30.2474
• 作为产物：
  描述：

  孕甾二醇 在 溶剂黄146 作用下， 生成 (20S)-20-hydroxy-5β-pregnan-3α-yl acetate 、 alkaline earth salt of/the/ methylsulfuric acid
  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

文献信息

• Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction
  作者：Eva Šťastná、Ivan Černý、Vladimír Pouzar、Hana Chodounská

  DOI：10.1016/j.steroids.2010.04.010

  日期：2010.10

  A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride reduction. The best results were obtained with the 2-keto derivative 1, 7-keto derivatives 5 and 6, and

  在氯化铈（III）或碘化sa（III）的存在下，用硼氢化钠还原一系列酮类固醇（Luche还原）。通过HPLC测定轴向和赤道醇的比例，并将结果与​​通过标准硼氢化钠还原获得的结果进行比较。用2-酮衍生物1、7-酮衍生物5和6以及12-酮衍生物8获得最好的结果，其中铈（III）离子的加入导致轴向/赤道比的倒置。20-酮衍生物11的卢氏还原将（20S）/（20R）醇的混合物中的（20S）-醇的比例从标准的硼氢化钠还原中的5％提高至35％。
• Azido analogs of neuroactive steroids
  作者：Lukáš Vidrna、Ivan Černý、Vladimír Pouzar、Jiřina Borovská、Vojtěch Vyklický、Ladislav Vyklický、Hana Chodounská

  DOI：10.1016/j.steroids.2011.04.008

  日期：2011.9

  Analogs of pregnanolone (3 alpha-hydroxy-5 beta-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17 alpha- and 17 beta-azido-5 beta-androstan-3 alpha-ol), compounds with its part replaced (20-azido-21-nor-5 beta-pregnan-3 alpha-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5 beta-pregnan-3 alpha-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound. (C) 2011 Elsevier Inc. All rights reserved.
• Heard; Hoffman; Mack, Journal of Biological Chemistry, 1944, vol. 155, p. 607,611
  作者：Heard、Hoffman、Mack

  DOI：——

  日期：——