3.17-Dioxo-6β,19-cyclo-Δ⁴-androsten | 2352-95-6

• 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: 3.17-Dioxo-6β,19-cyclo-Δ⁴-androsten
• 英文别名: 3.17-Dioxo-6β,19-cyclo-androsten-(4)；3,17-Dioxo-6β,19-cyclo-androst-4-en；6β,19-Cycloandrost-4-en-3,17-dion；(1S,2S,5S,9S,10R,12S)-5-methylpentacyclo[10.5.1.01,13.02,10.05,9]octadec-13-ene-6,15-dione
• CAS: 2352-95-6
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: JBQSHZPQJIKKGY-HYCFJWNYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  455.6±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3.17-Dioxo-6β,19-cyclo-Δ⁴-androsten 在 Lindlar's catalyst 甲烷磺酸 、 氢气 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 生成 (3aS,3bR,10aR,10bS,12aS)-12a-Methyl-2,3,3a,3b,4,5,6,9,10,10a,10b,11,12,12a-tetradecahydro-benzo[3,4]cyclohepta[1,2-e]indene-1,8-dione
  参考文献：
  名称：

  Solvolyse von 3,17-Dioxo-19-mesyloxy-?4-androsten. �ber Steroide, 216. Mitteilung

  摘要：

  Abstract3,17‐Dioxo‐19‐mesyloxy‐Δ4‐androstene was reacted with lithiumchloride in isopropanol. In addition to the mainly formed 3,17‐dioxo‐19‐chloro‐Δ4‐androstene two side products were isolated and identified as 6ß‐methylestrone and 3,17‐dioxo‐B‐homo‐Δ4,6‐19‐norandrostadiene.

  DOI：

  10.1002/hlca.19690520212
• 作为产物：
  描述：

  ((8R,9S,10S,13S,14S)-13-methyl-3,17-dioxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-10H-cyclopenta[a]phenanthren-10-yl)methyl 4-methylbenzenesulfonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3.17-Dioxo-6β,19-cyclo-Δ⁴-androsten
  参考文献：
  名称：

  类固醇 cclix11Part CCLVIII。J. Romo、L. Rodriguez-Hahn、P. Joseph-Nathan、M. Martínez 和 P. Crabbe。公牛。Soc.Chim。法国（提交出版）.. 5β,19 和 6β,19-环类固醇的合成

  摘要：

  摘要 3β,19-dihydroxyandrost-5-ene-17-one-3-acetate 19-tosylate (Ib) 的溶剂分解产生了 Δ6-5, 19-环类固醇 IIa 或各种 6α-取代的 5,19-环丙烷 V 取决于反应条件。讨论了这些反应通过中间同烯丙基桥接阳离子进行的可能性。描述了从 19-羟基雄甾醇-4-烯 3,17-二酮甲苯磺酸酯 (VIb) 形成 6β,19-环丁烷

  DOI：

  10.1016/0039-128x(64)90022-4

文献信息

• Steroids cclix11Part CCLVIII. J. Romo, L. Rodriguez-Hahn, P. Joseph-Nathan, M. Martínez and P. Crabbe. Bull. Soc.Chim. France (submitted for publication).. The synthesis of 5β,19 and 6β,19-cyclo steroids
  作者：O. Halpern、P. Crabbé、A.D. Cross、I. Delfin、L. Cervantes、A. Bowers

  DOI：10.1016/0039-128x(64)90022-4

  日期：1964.7

  Abstract The solvolysis of 3β,19-dihydroxyandrost-5-ene-17-one-3-acetate 19-tosylate (Ib) led to the Δ6-5, 19-cyclo steroid IIa or a variety of 6α-substituted 5,19-cyclopropanes V depending upon the reaction conditions. The possibility that these reactions proceed through an intermediate homoallylic bridged cation is discussed. The formation of 6β,19-cyclobutanes from 19-hydroxyandrost-4-ene 3,17-dione

  摘要 3β,19-dihydroxyandrost-5-ene-17-one-3-acetate 19-tosylate (Ib) 的溶剂分解产生了 Δ6-5, 19-环类固醇 IIa 或各种 6α-取代的 5,19-环丙烷 V 取决于反应条件。讨论了这些反应通过中间同烯丙基桥接阳离子进行的可能性。描述了从 19-羟基雄甾醇-4-烯 3,17-二酮甲苯磺酸酯 (VIb) 形成 6β,19-环丁烷
• Steroide und Sexualhormone 228. Mitteilung. Zu Solvolyseversuchen mit ?4- und ?5-unges�ttigten 19-Mesyloxy-Steroiden. (Vorl�ufige Mitteilung)
  作者：J. J. Bonet、H. Wehrli、K. Schaffner

  DOI：10.1002/hlca.19620450731

  日期：——

  Solvolysis of 3,17-Dioxo-19-mesyloxy-Δ4-androstene (2) in methanolic sodium methylate solution yields a mixture of the 6β, 19-cyclo-androstane derivatives 3 and 4. 3,17-Diethylenedioxy-19-mesyloxy-Δ5-androstene (11) in boiling pyridine is converted into 3,17-diethylenedioxy-5β, 19-cyclo-Δ6-androstene (12).

  的3,17-二氧代-19-甲磺酰氧基-Δ溶剂解4雄甾（2）在甲醇钠的甲醇溶液产生的6β，19 -环-雄甾烷衍生物的混合物3和4。3,17- Diethylenedioxy -19-甲磺酰氧基-Δ 5雄甾（11）在沸腾的吡啶被转化成3,17- diethylenedioxy-5β，19-环Δ 6雄甾（12）。
• Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules
  作者：Wei-Sheng Tian、Zhen Lei、Ling Chen、Ying Huang

  DOI：10.1016/s0022-1139(99)00175-x

  日期：2000.2

  The reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal ketones and alkenyl halides as well as 19-hydroxyl steroids were studied in detail. Utilizing these reactions, some steroidal molecules with the biological activity or structurally unique properties have been synthesized.

  详细研究了聚（全）氟烷磺酰氟与类固醇酮和烯基卤化物以及19-羟基类固醇的反应。利用这些反应，已经合成了具有生物活性或结构独特性质的一些甾体分子。
• Steroide und Sexualhormone. 229. Mitteilung. Herstellung von B-Homo-6,10-cyclo-19-nor-androstan-Verbindungen. (Vorläufige Mitteilung)
  作者：J. J. Bonet、H. Wehrli、K. Schaffner

  DOI：10.1002/hlca.19630460536

  日期：——

  The smooth conversion of the 3, 17-dioxo-6β, 19-cyclo-androstane derivatives 3 and 4 into the 3, 17-dioxo-Δ4-B-homo-1, 10-cyclo-19-nor-androstene 5 is described.

  平滑转换3,17二氧代6β，19 -环-雄甾烷衍生物的3和4到3，17二氧代Δ 4 -B-HOMO-1，10-环-19-降-雄甾5是描述。
• 6β,19-Bridged androstenedione analogs as aromatase inhibitors
  作者：Sachiko Komatsu、Ayaka Yaguchi、Kouwa Yamashita、Masao Nagaoka、Mitsuteru Numazawa

  DOI：10.1016/j.steroids.2009.06.001

  日期：2009.11

  Inhibition of aromatase is an efficient approach for the prevention and treatment of breast cancer. New 6 beta,19-bridged steroid analogs of androstenedione, 6 beta,19-epithio- and 6 beta,19-methano compounds 11 and 17, were synthesized starting from 19-hydroxyand rostenedione (6) and 19-formylandrost-5-ene-3 beta,17 beta-yl diacetate (12), respectively, as aromatase inhibitors. All of the compounds including known steroids 6 beta,19-epoxyandrostenedione (4) and 6 beta,19-cycloandrostenedione (5) tested were weak to poor competitive inhibitors of aromatase and, among them, 6 beta,19-epoxy steroid 4 provided only moderate inhibition (K-i: 2.2 mu M). These results show that the 6 beta,19-bridged groups of the inhibitors interfere with binding in active site of aromatase. (C) 2009 Elsevier Inc. All rights reserved.