pregn-4-en-3-one | 1232-18-4

• 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: pregn-4-en-3-one
• 英文别名: 4-pregnen-3-one；Pregn-4-en-3-on；(8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1232-18-4
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: AYGFEWYXKDFVIQ-NWSAAYAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  pregn-4-en-3-one 在 palladium on activated charcoal 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 N-环己基异丙基胺 、 氢气 、 四氯苯醌 、 对甲苯磺酸 、 苯甲醚 、 菲醌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 58.5h， 生成 2,17-dimethyl-18,19-dinor-17α-pregna-1,3,5,7,9,11,13-heptaene
  参考文献：
  名称：

  Synthesis of triaromatic steroid hydrocarbons methylated at position 2, 3 or 6: molecular fossils of yet unknown biological origin

  摘要：

  C-21-29 triaromatic steroid hydrocarbons bearing a methyl group at unusual positions 2, 3 or 6 have been synthesized from pregnenolone, cholesterol or stigmasterol via stera-3,5-dienes. Their occurrence in various sedimentary rocks and petroleums suggests the presence of yet unknown biological precursors.

  DOI：

  10.1016/s0040-4020(01)80848-6
• 作为产物：
  描述：

  孕烯醇酮 在 氢氧化钾 、 aliminium tert-butylate 、 一水合肼 作用下， 以 丙酮 、 甲苯 、 正丁醇 、 二乙二醇 为溶剂， 反应 17.0h， 生成 pregn-4-en-3-one
  参考文献：
  名称：

  Synthesis of triaromatic steroid hydrocarbons methylated at position 2, 3 or 6: molecular fossils of yet unknown biological origin

  摘要：

  C-21-29 triaromatic steroid hydrocarbons bearing a methyl group at unusual positions 2, 3 or 6 have been synthesized from pregnenolone, cholesterol or stigmasterol via stera-3,5-dienes. Their occurrence in various sedimentary rocks and petroleums suggests the presence of yet unknown biological precursors.

  DOI：

  10.1016/s0040-4020(01)80848-6

文献信息

• [EN] PROCESS FOR PREPARATION OF DYDROGESTERONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DU DYDROGESTÉRONE
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2018109622A1

  公开（公告）日：2018-06-21

  The present invention relates to process for the preparation of dydrogesterone.

  本发明涉及一种制备去甲孕酮的方法。
• Steroids and Steroidases. XVI. An Evaluation of Synthetic Routes to Variously C-17-Substituted Δ⁵-3-Ketosteroids
  作者：J. Bryan Jones、Keith D. Gordon

  DOI：10.1139/v72-435

  日期：1972.8.15

  Several routes to variously C-17-substituted Δ5-3-ketosteroids have been surveyed. The most convenient method was found to be oxidation of Δ5-3β-alcohol precursors with the Collins reagent, dipyridine chromium trioxide in methylene chloride. The purities of the desired acid- and base-labile compounds obtained were ≥ 99% in each case.

  已经研究了几种不同的 C-17 取代的 Δ5-3-酮类固醇的途径。发现最方便的方法是用柯林斯试剂氧化 Δ5-3β-醇前体，二吡啶三氧化铬在二氯甲烷中。在每种情况下，所获得的所需酸和碱不稳定化合物的纯度均≥ 99%。
• METHOD FOR MEASURING AROMATASE ACTIVITY
  申请人：WHATELEY JOHN GERARD

  公开号：US20110014641A1

  公开（公告）日：2011-01-20

  The present invention relates to compounds useful for measuring aromatase activity. The invention further provides methods for measuring aromatase activity and for screening test agents which modulate aromatase activity. A kit is also provided for use in such screening methods.

  本发明涉及用于测量芳香化酶活性的化合物。本发明还提供了测量芳香化酶活性和筛选调节芳香化酶活性的试剂的方法。还提供了用于这种筛选方法的试剂盒。
• 17-Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes, their pharmaceutical use and processes for their preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004773A2

  公开（公告）日：1979-10-17

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula: wherein X' is fluoro, chloro or bromo; X2 is fluoro, chloro or hydrogen; X3 is fluoro, chloro, bromo or hydrogen; X4 is =C=O or or may also be when X3 is chloro; R is alkyl or 1 to 6 carbon atoms or phenyl or benzyl optionally substituted with one substituent on the phenyl ring chosen from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl, or OR' and R2 together are isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or a single bond; are useful as anti-inflammatory agents. They can be prepared by treating the corresponding 17β-carboxylic acid with a suitable base salt of RSH. The 17β-hydroxy compounds can be esterified to produce the 17β-alkanoyloxy compound. The double bond at the 4,5 position can be produced by contacting the corresponding Δ5 compound with a base.

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula： 其中 X' 是氟、氯或溴； X2 是氟、氯或氢 X3 是氟、氯、溴或氢； X4 是 =C=O 或 或也可以是 当 X3 为氯时； R 是 1 至 6 个碳原子的烷基或苯基或苄基，可选择被苯基环上的一个取代基取代，该取代基可从 1 至 4 个碳原子的烷基、1 至 4 个碳原子的烷氧基和卤素组成的组中选择； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR' 和 R2 合在一起为异亚丙基二氧基；以及 C-1 和 C-2 之间的实线和断线代表双键或单键； 可用作抗炎剂。它们可以通过将相应的 17β- 羧酸与合适的 RSH 碱盐进行处理来制备。17β-hydroxy 化合物经酯化后可生成 17β-alkanoyloxy 化合物。4,5 位的双键可通过将相应的 Δ5 化合物与碱接触而生成。
• Thio etianic acid derivatives, their preparation and pharmaceutical use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004741A2

  公开（公告）日：1979-10-17

  Thio etianic acid derivatives of the formula wherein X' is hydrogen, fluoro, or chloro; X2 is hydrogen, fluoro, chloro or bromo; X3 is =C=O Cl may also be =C when X2 is chloro; H R is alkyl of 1 to 6 carbon atoms, or phenyl or benzyl optionally substituted with a substituent on the phenyl ring which is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon _ atoms or halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl or OR1 and R2 together are 16a, 17a-isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or single bond; are useful an anti-inflammatory steroids. They can be prepared by reacting the corresponding 17β-carboxylic acid or a reactive derivative thereof with an alkali metal salt of RSH.

  式中的硫代乙酸衍生物 式中 X'是氢、氟或氯 X2 是氢、氟、氯或溴 X3 是 =C=O Cl 当 X2 为氯时，也可以是 =C；H R 是 1 至 6 个碳原子的烷基，或苯基或苄基，可选择被苯基环上的 1 至 4 个碳原子的烷基、1 至 4 个碳 _ 原子的烷氧基或卤素取代； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR1 和 R2 一起为 16a、17a-异亚丙基二氧基；C-1 和 C-2 之间的实线和断线代表双键或单键。它们可以通过相应的 17β 羧酸或其活性衍生物与 RSH 的碱金属盐反应来制备。