11alpha,17beta-二羟基-17-甲基雄甾-4-烯-3-酮 | 1807-02-9

• 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: 11alpha,17beta-二羟基-17-甲基雄甾-4-烯-3-酮
• 英文名称: 11α,17β-Dihydroxy-17α-methylandrost-4-en-3-one
• 英文别名: 11α-hydroxy-17α-methyltestosterone；11α-hydroxymethyltestosterone；11α,17β-dihydroxy-17α-methyl-androst-4-en-3-one；11α,17β-Dihydroxy-17α-methyl-androst-4-en-3-on；(11α,17β)-11,17-dihydroxy-17-methyl-androst-4-en-3-one；11α,17β-dihydroxy-17-methylandrost-4-en-3-one；11alpha,17beta-Dihydroxy-17-methylandrost-4-en-3-one；(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 1807-02-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: UBIBSXMTVJAYTQ-QMNUTNMBSA-N

物化性质

• 熔点：
  160-162 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  475.5±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  11alpha,17beta-二羟基-17-甲基雄甾-4-烯-3-酮 在 乙醇 、 sodium formate 作用下， 生成 甲睾酮
  参考文献：
  名称：

  SYNTHESIS OF POTENT ORAL ANABOLIC-ANDROGENIC STEROIDS

  摘要：

  DOI：

  10.1021/ja01583a072
• 作为产物：
  描述：

  17-甲睾酮 生成 11alpha,17beta-二羟基-17-甲基雄甾-4-烯-3-酮
  参考文献：
  名称：

  ZAKELJ-MAVRIC, M.;BELIC, I., J. STEROID BIOCHEM., 28,(1987) N 2, 197-201

  摘要：

  DOI：

文献信息

• Efficient Preparation of Alkoxymethyl Carbonates by Using Potassium Carbonate, Chloromethyl Alkyl Ethers, and Alcohols
  作者：Katsunori Teranishi、Atsuko Komoda、Makoto Hisamatsu、Tetsuya Yamada

  DOI：10.1246/bcsj.68.309

  日期：1995.1

  A synthesis of new “alkoxymethyl carbonate” is presented starting with alcohol. In the presence of potassium carbonate, primary alcohols react with chloromethyl alkyl ethers in N,N-dimethylformamide under mild conditions to give the corresponding alkoxymethyl carbonates in good yields without giving the alkoxymethyl ethers. The yield of alkoxymethyl carbonate is seriously effected by reaction solvent

  以醇为原料合成了新的“烷氧基甲基碳酸酯”。在碳酸钾的存在下，伯醇与氯甲基烷基醚在 N,N-二甲基甲酰胺中在温和条件下反应，以良好的收率得到相应的烷氧基甲基碳酸酯，而不会生成烷氧基甲基醚。烷氧基甲基碳酸酯的收率受反应溶剂的影响很大，本方法不适用于叔醇。甲氧基甲基碳酸酯可以在温和的碱性或酸性条件下容易地去除，并且在碱性条件下进行甲氧基甲醇基团的选择性醇盐交换。
• One-Step Synthesis of Novel Carbonates: Alkoxymethyl Carbonates, from Alcohols and Chloromethyl Alkyl
  作者：Katsunori Teranishi、Hidekazu Nakao、Atsuko Komoda、Makoto Hisamatsu、Tetsuya Yamada

  DOI：10.1055/s-1995-3874

  日期：1995.2

  A synthesis of the novel carbonates, alkoxymethyl carbonates, is presented, starting with an alcohol. In the presence of silver carbonate, primary and secondary alcohols react with chloromethyl alkyl ethers in N,N-dimethylformamide under mild conditions to give the corresponding alkoxymethyl carbonates in good yields, without forming the alkoxymethyl ethers. The yields of alkoxymethyl carbonates are heavily influenced by the reaction solvent and this method is not applicable to tertiary alcohols. Methoxymethyl carbonate can be removed readily under mild basic or acidic conditions, and selective alkoxide interchange of the methoxymethoxide group occurs under basic conditions.

  本文介绍了一种新型碳酸酯——烷氧甲基碳酸酯的合成，反应以醇为起始物。在银碳酸盐的存在下，初级和次级醇在温和条件下与氯甲基烷基醚在N,N-二甲基甲酰胺中反应，生成相应的烷氧甲基碳酸酯，且不生成烷氧甲基醚。烷氧甲基碳酸酯的产率受到反应溶剂的强烈影响，并且该方法不适用于三级醇。甲氧基甲基碳酸酯在温和的碱性或酸性条件下可以方便地去除，且在碱性条件下甲氧基甲氧化物基团会发生选择性的烷氧基互换。
• Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone
  作者：Tomasz Janeczko、Jarosław Popłoński、Ewa Kozłowska、Monika Dymarska、Ewa Huszcza、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.bioorg.2018.03.021

  日期：2018.8

  and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various

  在这项工作中，芥蓝KCh 93，Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-，12β-，7α-，11α-，15α羟基衍生物与分别为44％，29％，6％，5％和9分％的收率。小号。总消旋体KCh 105提供7α-，15α-和11α-羟基衍生物，产率分别为45％，19％和17％。毛毛虫sp。KCh 6651提供15α-，11α-，7α-，6β-，9α-，14α-羟基和6β，14α-二羟基衍生物，产率分别为31％，20％，16％，7％，5％，7％和4 ％， 分别。确定了14α-羟基和6β，14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响，但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用，但没有改变所得产物的百分比组成。
• Process for the preparation of 4-amino-.DELTA..sup.4 -3-ketosteroids via
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05965550A1

  公开（公告）日：1999-10-12

  The invention discloses 3-ketosteroids of the following formula used to inhibit steroid C.sub.17-20 lyase: ##STR1## wherein R is OH, C.sub.1 -C.sub.6 alkanoyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.4 alkanol, COCH.sub.2 OH, CO.sub.2 H, CONR.sub.7 R.sub.8, cyclopropyloxy, cyclopropylamino, acetylthioalkane, 2,2-dimethyldioxolan4-yl, 1,2-dihydroxyethyl and C.sub.1-4 alkylthiol; R.sub.1 is hydrogen, hydroxy or C.sub.1-6 alkyl; R and R.sub.1 together may indicate .dbd.O, that is an oxygen double bonded to the 17 carbon; R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl; R.sub.5 and R.sub.6 are each independently hydrogen or OH; R.sub.5 and R.sub.6 together may indicate .dbd.O, that is an oxygen double bonded to the 11 carbon; R.sub.7 is hydrogen or C.sub.1 -C.sub.8 alkyl; R.sub.8 is C.sub.1 -C.sub.8 alkyl; and with the proviso that, when R is OH, then R.sub.1 is hydrogen; and with the proviso that, when R.sub.5 is OH, then R.sub.6 is hydrogen.

  该发明揭示了以下公式的3-酮类固醇，用于抑制类固醇C.sub.17-20裂解酶：其中R为OH，C.sub.1-C.sub.6烷酰基，C.sub.1-C.sub.6烷酰氧基，C.sub.1-C.sub.4烷醇，COCH.sub.2OH，CO.sub.2H，CONR.sub.7R.sub.8，环丙氧基，环丙基氨基，乙酰硫代烷，2,2-二甲基二氧杂环戊烷-4-基，1,2-二羟乙基和C.sub.1-4烷基硫醇；R.sub.1为氢，羟基或C.sub.1-6烷基；R和R.sub.1一起可能表示.dbd.O，即与第17碳形成氧双键；R.sub.2，R.sub.3和R.sub.4分别独立地为氢或C.sub.1-C.sub.6烷基；R.sub.5和R.sub.6分别独立地为氢或OH；R.sub.5和R.sub.6一起可能表示.dbd.O，即与第11碳形成氧双键；R.sub.7为氢或C.sub.1-C.sub.8烷基；R.sub.8为C.sub.1-C.sub.8烷基；并且在R为OH时，R.sub.1为氢；在R.sub.5为OH时，R.sub.6为氢。
• Photochemistry of Steroid 4-en-3-one 11α-Nitrites. A Novel Synthesis of A-Nor-B-homo Steroids
  作者：Hans Reimann、Olga Z. Sarre

  DOI：10.1139/v71-057

  日期：1971.1.15

  Photolysis of some 11 α-hydroxysteroid 4-en-3-one nitrites afforded 1-oximinosteroid 4-en-3-ones and 9a-methyl-B(9a)-homo-A-norsteroid 3(5),9a-dien-2-ones. Chemical and physical evidence for the latter, as well as a plausible mechanism for the transformation, is presented.

  对一些11α-羟基类固醇4-烯-3-酮硝酸酯进行光解反应，得到了1-肟基类固醇4-烯-3-酮和9a-甲基-B（9a）-同型-A-去甲类固醇3（5），9a-二烯-2-酮。本文提供了后者的化学和物理证据，以及可能的转化机理。