2β,3α-dihydroxy-5α-androst-17-one | 83808-48-4

• 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
• 英文名称: 2β,3α-dihydroxy-5α-androst-17-one
• 英文别名: 2β,3α-dihydroxy-5α-androstan-17-one；2β,3α-dihydroxy-5α-androstanone-(17)；2β,3α-Dihydroxy-5α-androstanon-(17)；5alpha-Androstane-2beta,3alpha-diol-17-one；(2S,3S,5S,8R,9S,10S,13S,14S)-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 83808-48-4
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: HILNXGBHRIVSOD-PPMYXAGCSA-N

物化性质

• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2β,3α-dihydroxy-5α-androst-17-one 在 sodium 作用下， 生成 2β,3α,17β-triacetoxy-5α-androstane
  参考文献：
  名称：

  Sterols. LXIII. 2,3-Dihydroxyandrostane Derivatives

  摘要：

  DOI：

  10.1021/ja01875a006
• 作为产物：
  描述：

  表雄酮 在 吡啶 、 三氟甲磺酸酐 、 硫酸 、 水 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2β,3α-dihydroxy-5α-androst-17-one
  参考文献：
  名称：

  从动力学控制到热力学控制的变化使得邻二醇的反式选择性立体化学编辑成为可能

  摘要：

  在这里，我们报道了顺式-1,2-二醇选择性催化异构化为反式-双赤道-1,2-二醇。该方法采用三苯基硅烷硫醇（Ph 3 SiSH）作为催化剂，并在光氧化还原催化剂存在下和蓝光照射下在温和条件下进行。该方法具有高度化学选择性、广泛的官能团耐受性，并且提供了使用其他方法不易获得的反式二醇产物的简洁途径。机理研究表明，异构化是通过硅烷硫醇催化剂介导的可逆氢原子转移途径进行的。

  DOI：

  10.1021/jacs.1c11902

文献信息

• METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS
  申请人：Ge Yu

  公开号：US20120214987A1

  公开（公告）日：2012-08-23

  The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5a-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.

  该发明涉及制备3α-O-连接类固醇的过程，包括3α-O-连接-雄烯类固醇和3α-O-连接-5α-雄烷类固醇。在一个过程中，3α,4α-环氧基雄-5-烯-17-酮主要在环氧基团处还原，其中3α,4α-环氧官能团的还原优先发生在C4位置，并保留C3位置的构型，以提供3α-O-连接-雄烯类固醇。在另一个过程中，通过Mitsunobu反应提供条件，使3β-羟基雄-5-烯类固醇的构型发生倒置，以提供含有减少量3α,5α-环雄烷副产物杂质的3α-O-连接-雄烯类固醇。
• Facile Synthesis of Steroidal Vicinal Hydroxysulfides via the Reaction of Steroidal Epoxides with Thiols in the Presence of an Ionic Liquid
  作者：Rita Skoda-Földes、Anita Horváth、Dávid Frigyes、Sándor Mahó、Zoltán Berente、László Kollár

  DOI：10.1055/s-0029-1217031

  日期：2009.12

  can be carried out effectively in the Brønsted acidic ionic liquid [Hmim]+[BF4]- as a recyclable solvent and catalyst. The use of other ionic liquids/molten salts resulted in a decrease in the conversion and/or in reduced selectivity. In [bmim]+Br-, a conversion of 2,3-epoxy-17-ones into 2,17- and 3,17-diones was also observed. catalysis - epoxides - ionic liquids - ring-opening - steroids - thiols

  可以在布朗斯台德酸性离子液体[Hmim] + [BF 4 ] -作为可循环利用的溶剂和催化剂中，有效地进行甾族2,3-环氧化物与硫醇的开环。使用其他离子液体/熔融盐会导致转化率降低和/或选择性降低。在[BMIM] +溴-，2,3-环氧-17-酮转化成2,17-和3,17-二酮，也观察到。 催化-环氧化物-离子液体-开环-类固醇-硫醇
• Facile ring opening of 2,3-epoxy-steroids with aromatic amines in ionic liquids
  作者：Anita Horváth、Rita Skoda-Földes、Sándor Mahó、Zoltán Berente、László Kollár

  DOI：10.1016/j.steroids.2006.04.006

  日期：2006.8

  Efficient ring opening of steroidal 2,3-epoxides with stoichiometric amount of aromatic amines has been carried out using an ionic liquid ([bmim](+)[BF4](-)) both as solvent and catalyst. The reactions were completely regio- and stereoselective in each case. The aminoalcohol products have chair conformations in ring A. The ionic liquid-mediated ring opening can efficiently be carried out with aliphatic amines like morpholine as well. (c) 2006 Elsevier Inc. All rights reserved.
• NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
  申请人：SAGE THERAPEUTICS, INC.

  公开号：US20150175651A1

  公开（公告）日：2015-06-25

  Described herein are neuroactive steroids of the Formula (1) or a pharmaceutically acceptable salt, solvate, stereoisomer, tautomer, and/or isotopic variant thereof. Such compounds are envisioned, in certain embodiments, to behave as soft drugs and, in certain embodiments, as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.
• A Change from Kinetic to Thermodynamic Control Enables <i>trans-</i>Selective Stereochemical Editing of Vicinal Diols
  作者：Yu-An Zhang、Xin Gu、Alison E. Wendlandt

  DOI：10.1021/jacs.1c11902

  日期：2022.1.12

  Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under blue light irradiation. The method is highly chemoselective, broadly functional group tolerant and provides concise access to trans-diol products

  在这里，我们报道了顺式-1,2-二醇选择性催化异构化为反式-双赤道-1,2-二醇。该方法采用三苯基硅烷硫醇（Ph 3 SiSH）作为催化剂，并在光氧化还原催化剂存在下和蓝光照射下在温和条件下进行。该方法具有高度化学选择性、广泛的官能团耐受性，并且提供了使用其他方法不易获得的反式二醇产物的简洁途径。机理研究表明，异构化是通过硅烷硫醇催化剂介导的可逆氢原子转移途径进行的。