<3aS-(3aα,9aα,9bβ)>-3a,4,5,9,9a,9b-hexahydro-3a,6-dimethyl-1H-benzindene-3,7(2H,8H)-dione | 10072-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <3aS-(3aα,9aα,9bβ)>-3a,4,5,9,9a,9b-hexahydro-3a,6-dimethyl-1H-benzindene-3,7(2H,8H)-dione
• 英文别名: (+)-Des-A-androst-9-en-5,17-dion
• CAS: 10072-75-0
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: DSUVUPKSEQHAGM-XUJVJEKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <3aS-(3aα,9aα,9bβ)>-3a,4,5,9,9a,9b-hexahydro-3a,6-dimethyl-1H-benzindene-3,7(2H,8H)-dione 在 sodium tetrahydroborate 、 lithium bromide 、 copper(ll) bromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 <3S(3α,3aα,9bβ)>-3a,6-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzindene-3,7-diol
  参考文献：
  名称：

  Antiandrogenic activity of a series of des-A-steroid derivatives

  摘要：

  In the search for new antiandrogens, a number of des-A-steroids were prepared by condensation of Grignard reagents with lactone 3. From the resulting key intermediates 5, various structural modifications were performed such as the introduction of an additional unsaturation to afford dienones 8 and aromatic derivatives 10 or the introduction of an alkyl substituent mostly in position 10 (11-13) but also in some cases in position 16 (22). In addition, 13-ethyl analogues were also prepared from lactone 4. The relative binding affinities (RBAs) for the androgen receptor of these compounds were determined under various conditions. Some compounds exhibit a capacity to interact with the receptor comparable to that of testosterone. One of the most potent compounds is 17beta-hydroxy-des-A-androsta-9,11-dien-5-one (8b), RBA value 73% of that of testosterone. More interestingly, several compounds were found to have an antiandrogenic profile in vitro and in vivo. One of the most effective compounds is 10-ethyl-17beta-hydroxy-des-A-estra-9-en-5-one (5c), which exhibits a strong local antiandrogenic activity in hamsters, without any significant systemic antiandrogenic effects. The corresponding 17beta-acetyl derivative (RU 38882) has been selected for extended pharmacological studies.

  DOI：

  10.1021/jm00150a009
• 作为产物：
  描述：

  (+/-)-2,3,3a,4,5,7,8,9,9aβ,9bα-Decahydro-3aβ,6-dimethyl-3β-hydroxy-7-oxo-1H-benzinden 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 <3aS-(3aα,9aα,9bβ)>-3a,4,5,9,9a,9b-hexahydro-3a,6-dimethyl-1H-benzindene-3,7(2H,8H)-dione
  参考文献：
  名称：

  Versuche zur Synthese von9β，10α-Steroiden; B，C，D三轮车Verbindungen †

  摘要：

  在该化合物的一种新的和有效的合成的搜索7，的环化5（由获得的迈克尔从-反应3和4）进行了研究。用强酸处理5可得到已知的二烯二酮8。温和的酸性条件使桥连的醇9和其他身份不明的产品，而不是所需的烯酮6。在基本条件下，5并没有环化为6，而是经历了Michael逆反应。然后尝试将二烯二酮8转化为14α-烯酮19。但是，催化加氢和锂氨还原反应均为8，主要产生14β产物。在一些氢化实验中，二烯二酮8异构化成苯酚13（主要）和14（次要）。通过化学和光谱法确定了新的异构体des-A-androst-9-en-5，17-二酮（16、17和20）的立体化学。

  DOI：

  10.1002/hlca.19700530512

文献信息

• Über Steroide. 120. Mitteilung. Totalsynthetische Versuche in der Steroidreihe IV. Zur Umwandlung von 6-Ring- in 5-Ring-Ketone
  作者：P. Wieland、G. Anner、K. Miescher

  DOI：10.1002/hlca.19530360717

  日期：——

  Es wird eine neue Ringverengerungs-Methode für D-Homo-steroide beschrieben. Sie beruht auf der Beckmann'schen Umlagerung von α-Isonitrosoketonen und Cyclisierung der erhaltenen Nitrilcarbonsäuren. Das Verfahren wird am Beispiel der Überführung des Δ8,14-1,7-Dioxo-8,11-dimethyl-dodecahydro-phenanthrens (I) ins 1-Oxo-cyclopenta[4,5-a]Δ5,10-6-oxo-2, 5-dimethyl-octahydro-naphtalin(XII) näher erläutert

  Es wird eine neue Ringverengerungs-Methode for D-Homo-steroide beschrieben。在贝克曼的著作《α-异亚硝基酮与环戊二烯的硝化碳》中发表。达斯Verfahren wird是Beispiel DERÜberführungDESΔ 8,14 -1,7-二氧代-8,11-二甲基十二氢phenanthrens（I）INS 1-氧代环戊二烯并[4,5-α]Δ 5,10 -6 -oxo-2、5-二甲基八氢萘酞（XII）的名称。
• Totalsynthese von Steroiden. 1. Mitteilung.<i>rac</i>-17β-Hydroxydes-A-androst-9-en-5-on
  作者：G. Saucy、R. Borer、A. Fürst

  DOI：10.1002/hlca.19710540734

  日期：1971.11.1

  AbstractIn connection with earlier work on the synthesis of 9β, 10α‐steroids, a new and practical synthesis of rac‐17α‐hydroxy‐des‐A‐androst‐9‐en‐5‐one (19) has been developed, based on a novel stereoselective condensation of 7‐hydroxy‐1‐nonen‐3‐one (3) with 2‐methyl‐cyclopentane‐1, 3‐dione (9) and subsequent transformations of the resulting tricyclic diene ether 12.
• Steroid Total Synthesis, Part II; (?)-17?-Hydroxy-des-A-androst-9-en-5-one
  作者：G. Saucy、R. Borer

  DOI：10.1002/hlca.19710540746

  日期：1971.11.1

  AbstractBased on the results obtained in the racemic series (part I), (—)‐17β‐hydroxy‐des‐A‐androst‐9‐en‐5‐one has been synthesized, starting with (S)‐(—)‐5‐heptanolide. The key step, viz. the condensation of (S)‐(—)‐7‐hydroxy‐1‐nonen‐3‐one (or its amine adduct) with 2‐methyl‐cyclopentane‐1, 3‐dione involves an asymmetric induction. Model experiments with (R)‐(+)‐5‐decanolide leading to the enantiomeric homolog of the BCD‐tricyclic compound are also described.
• Daniewski, Andrzej Robert; Piotrowska, Emilia; Wojciechowska, Wanda, Liebigs Annalen der Chemie, 1989, p. 1061 - 1064
  作者：Daniewski, Andrzej Robert、Piotrowska, Emilia、Wojciechowska, Wanda

  DOI：——

  日期：——
• DE954248
  申请人：——

  公开号：——

  公开（公告）日：——