3β-hydroxy-5α-androstane-6,17-dione | 4601-47-2

• 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: 3β-hydroxy-5α-androstane-6,17-dione
• 英文别名: androstan-3β-ol-6,17-dione；6-ketoepiandrosterone；3β-Hydroxy-5α-androstan-6,17-dion；3b-hydroxy-5a-androstane-6,17-dione；3α-Hydroxy-5α-androstandion-(6,17)；3beta-Hydroxy-5alpha-androstane-6,17-dione；(3S,5S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-6,17-dione
• CAS: 4601-47-2
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: HMFQSUMWKTYRNZ-ZTWNCRQDSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  453.4±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5α-androstane-6,17-dione 在 三氧化硫吡啶 、 碳酸氢钠 作用下， 以 苯 、 水 为溶剂， 反应 12.0h， 以95%的产率得到
  参考文献：
  名称：

  Requirements for Selective Hydrophobic Acceleration in the Reduction of Ketones

  摘要：

  Reductions of various quaternized hydrophobic beta-keto amines were performed in water and in methanol using borohydride anions carrying hydrophobic groups. The most important requirement of the substrate to permit hydrophobically accelerated selective reductions is the ability of the hydrophobic group of the substrate and its attached keto group to attain a coplanar relationship. Some derivatives of naturally occurring steroid diones have also been employed as substrates to probe the mechanism and utility of these hydrophobically accelerated selective reductions further.

  DOI：

  10.1021/ol0481481
• 作为产物：
  描述：

  去氢表雄酮 在 咪唑 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3β-hydroxy-5α-androstane-6,17-dione
  参考文献：
  名称：

  Requirements for Selective Hydrophobic Acceleration in the Reduction of Ketones

  摘要：

  Reductions of various quaternized hydrophobic beta-keto amines were performed in water and in methanol using borohydride anions carrying hydrophobic groups. The most important requirement of the substrate to permit hydrophobically accelerated selective reductions is the ability of the hydrophobic group of the substrate and its attached keto group to attain a coplanar relationship. Some derivatives of naturally occurring steroid diones have also been employed as substrates to probe the mechanism and utility of these hydrophobically accelerated selective reductions further.

  DOI：

  10.1021/ol0481481

文献信息

• Regioselective Oxidation of Steroids by a Manganese Porphyrin Carrying Metal Coordinating Groups
  作者：Sandro Belvedere、Ronald Breslow

  DOI：10.1006/bioo.2001.1215

  日期：2001.10

  A manganese porphyrin having four 2,2'-bipyridyl groups on its meso positions was synthesized. In the presence of Cu2+ ions it catalyzes the regioselective oxidation of steroid substrates carrying auxiliary metal coordinating groups.

  合成了在其内消旋位置具有四个2,2'-联吡啶基的锰卟啉。在Cu 2+离子的存在下，它催化带有辅助金属配位基团的类固醇底物的区域选择性氧化。
• Trimethylsilyl tetrafluoroborate a convenient reagent for solvolysis reactions
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo、Ernest Wenkert

  DOI：10.1016/s0040-4039(00)99942-8

  日期：1984.1

  Conversions of cyclopropyl carbinols (or their acetates) and ketones into homoallyl and γ-substituted ketone derivatives, respectively, are accomplished by trimethylsilyl tetrafluoroborate efficiently and under mild conditions.

  环丙基甲醇（或它们的乙酸盐）和酮分别通过高效四氟硼酸三甲基甲硅烷基酯在温和的条件下转化为均烯丙基和γ-取代的酮衍生物。
• Brassinosteroids: Synthesis and Activity of Some Fluoro Analogues
  作者：Barbora Slavikova、Ladislav Kohout、Milos Budesinsky、Jana Swaczynova、Alexander Kasal

  DOI：10.1021/jm800085p

  日期：2008.7

  using standard operations (reaction of 3beta-alcohols with (diethylamino)sulfur trifluoride, cleavage of epoxide with HF in py or BF 3.Et 2O). The 5alpha-fluorine was found to affect chemical reactivity (e.g., electrophilic addition to the Delta (2)-double bond) as well as physical properties (e.g., NMR, chromatographic behavior) of the products. Cytotoxicity of the products was studied using human normal

  使用标准操作（3β-醇与（二乙氨基）三氟化硫的反应，裂解）制备了三种类型的油菜素内酯的5α-雄甾烷和麦角甾烷类似物，它们在3α或5α位置或3α和5α位置含有氟原子。在py或BF 3.Et 2O中含HF的环氧化物）。发现5α-氟会影响产品的化学反应性（例如，对Delta（2）-双键的亲电加成）以及物理性质（例如，NMR，色谱行为）。使用人类正常细胞和癌细胞系，以28-homocastasterone作为阳性对照，研究了产品的细胞毒性，并使用以24-表油菜素内酯为标准的豆第二节间试验确定了它们的油菜素内酯型活性。在某些活性化合物中观察到F和OH基团的等效性。抗癌活性和油菜素内酯型活性彼此不相关：前者测试中麦角甾烷衍生物活性最高，而后者则雄甾烷酮衍生物最佳。
• Modified aromatase inhibitors having improved bioavailability
  申请人：Kneller W. Bruce

  公开号：US20050203074A1

  公开（公告）日：2005-09-15

  The present invention relates to the modification of 3-beta-hydroxyandrost-4-ene-6,17-dione (“3-OHAT”) and its metabolites/derivatives at either the 3 rd or 17 th carbon or 3 rd and 17 th carbons with various ethers and/or esters and to the modification of 3-beta-hydroxyandrost-4-ene-6,17-dione (“3-OHAT”) and its metabolites/derivatives at carbon 6 with a methyl, methoxy, methylene, hydroxymethylene or acetoxy functional group to improve and increase the oral bioavailability and/or plasma half life and/or efficacy in mammals.

  本发明涉及对 3-beta-羟基雄甾-4-烯-6,17-二酮（"3-OHAT"）及其代谢物/衍生物在第 3 或 或 碳或 碳或 3 第 和第 17 碳 3-OHAT"）及其代谢物/衍生物的第 6 碳上的甲基、甲氧基、亚甲基、羟甲基或乙酰氧基官能团，以改善和提高哺乳动物的口服生物利用度和/或血浆半衰期和/或药效。
• Direct Introduction of Oxygen into the Steroid Nucleus. II. Chromic Anhydride Oxidation of Isoandrosterone Acetate and Androstanediol Diacetate
  作者：H. B. MacPhillamy、C. R. Scholz

  DOI：10.1021/ja01141a085

  日期：1952.11