(8R,9S,13S,14S,17S)-13-乙基-3-甲氧基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-17-醇 | 848-01-1

• 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
• 中文名称: (8R,9S,13S,14S,17S)-13-乙基-3-甲氧基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-17-醇
• 英文名称: D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-trien-17β-ol
• 英文别名: (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene；(8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 848-01-1；3625-82-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: CNPGMVAEOUQDBN-SLHNCBLASA-N

物化性质

• 熔点：
  126-130 °C
• 沸点：
  441.4±45.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)
• 溶解度：
  溶于乙酸乙酯、甲醇、THF
• LogP：
  5.24 at 25℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17S)-13-乙基-3-甲氧基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-17-醇 在 盐酸 、 氨 、 lithium 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 环己酮 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 生成 左炔诺孕酮
  参考文献：
  名称：

  Synthesis of 13-alkyl-gon-4-ones

  摘要：

  描述了通过新的全合成方法制备13-甲基孕-4-烯和新型13-聚碳烷基孕-4-烯。通过形成在1,3,5(10),9(11)和14-位置不饱和的四环孕烷结构，选择性地在B和C环中还原，并将所产生的芳香A环化合物转化为孕-4-烯，制备具有孕激素、合成激素和雄激素活性的13-烷基孕-4-烯。

  公开号：

  US03959322A1
• 作为产物：
  描述：

  左炔诺孕酮 在 氢氧化钾 、 Celite 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (8R,9S,13S,14S,17S)-13-乙基-3-甲氧基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-17-醇
  参考文献：
  名称：

  Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids

  摘要：

  Two preparative chemical methods for aromatization of 19-nor-Delta(4)-3-oxosteroids are described. The first method consists of an oxidative aromatization of 19-nor-Delta(4)-3-oxosteroids with iodine-eerie ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Delta(9,11) derivative, the 6-oxo derivative as well as some ring-A iodinated material. Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation. Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product. In the second method, reaction of 19-nor-Delta(4)-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields. The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Delta(4,6)-3-oxosteroid.

  DOI：

  10.1016/0039-128x(94)90017-5

文献信息

• Synthesis of gon-4-enes
  申请人：Smith; Herchel

  公开号：US04002746A1

  公开（公告）日：1977-01-11

  1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17.alpha.-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.

  一种具有孕激素活性的治疗组合物，其活性成分为17-脂肪族羧酸酯的17α-乙炔基-18-甲基-19-去甲睾酮，以及用于该化合物的药用载体。
• Syntheses of Racemic and Optically Active 13β-Ethylgonanes.
  作者：Kentaro Hiraga

  DOI：10.1248/cpb.13.1289

  日期：——

  During the course of the synthesis of 18-methylestradiol 3-methyl ether, steric effect caused by the methyl group at 18-position was observed. It was found that ethylenediamine was a good solvent for the ethynylation reaction of the hindered ketone. Racemic and optically active 17β-hydroxy-13β, 17α-diethylgon-4-en-3-one were synthesized from 1-vinyl-6-methoxy-1-tetralol and 2-ethyl-1, 3-cyclopentanedion. The dextrorotatory diethylgonenone as well as the corresponding racemic diethylgonenone showed strong anabolic activities, whereas the levorotatory compound had no biological activity.

  在合成 18-甲基雌二醇 3-甲醚的过程中，观察到 18 位上的甲基产生了立体效应。研究发现，乙二胺是受阻酮乙炔化反应的良好溶剂。由 1-乙烯基-6-甲氧基-1-四氢萘酚和 2-乙基-1，3-环戊二酮合成了外消旋和光学活性的 17β-羟基-13β，17α-二乙基贡-4-烯-3-酮。右旋二乙基庚烯酮和相应的外消旋二乙基庚烯酮显示出很强的合成代谢活性，而左旋化合物则没有生物活性。
• Steroid sulfamates, method for the production and use thereof
  申请人：id pharma GmbH

  公开号：US06339079B1

  公开（公告）日：2002-01-15

  A novel class of gonane type and D-homo-gonane type steroids having sulfatase-inhibiting and/or estrogenic activity is presented for application in the pharmaceutical industry. The number and location of sulfamoyloxy groups on the steroids provides for sulfatase inhibiting and estrogenic activities that independently vary over a wide range, allowing the customization of the pharmaceutical for specific purposes, including treatment and diagnosis of estrogen-dependent tumors.

  提出了一种新型的戈南型和D-同型戈南型类固醇，具有抑制磺酸酯酶和/或雌激素活性，可应用于制药行业。类固醇上磺酰氧基团的数量和位置提供了磺酸酯酶抑制和雌激素活性，可独立地在广泛范围内变化，允许为特定目的定制药物，包括治疗和诊断雌激素依赖性肿瘤。
• Synthesis of A-ring aromatic steroids
  申请人：Hoffmann-La Roche Inc.

  公开号：US03933870A1

  公开（公告）日：1976-01-20

  Total synthesis of steroids of the estrone and equilenin series involving conjugate 1,4-addition of a meta-substituted benzyl organometallic reagent to a C/D bicyclic methylene ketone. An aromatization of the B-ring of .DELTA. 9(11) estrone derivatives.

  合成骑马甾酮和雌甾醇系列类固醇的总合成，包括将一个间位取代苄基有机金属试剂与C/D双环甲基酮进行共轭1,4-加成。对.DELTA.9(11)雌甾酮衍生物B环的芳构化。
• USE OF alpha,beta -UNSATURATED CARBONYL COMPOUNDS AS QUENCH REAGENTS FOR THE BIRCH REDUCTION
  申请人：ORTMANN Ingo

  公开号：US20080300428A1

  公开（公告）日：2008-12-04

  Use of α,β-unsaturated carbonyl compounds as quench reagents for the Birch reduction.

  α,β-不饱和羰基化合物作为Birch还原的淬灭试剂的应用。