(17E)-17-ethylidene-3-methoxy-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthrene

• 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: (17E)-17-ethylidene-3-methoxy-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthrene
• 化学式: C₂₀H₂₆O
• 分子量: 282.4
• InChiKey: OPBGYBSBTMYKEG-QLKAYGNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

文献信息

• [EN] NOVEL PROCESS AND INTERMEDIATE FOR PREPARATION OF ULIPRISTAL<br/>[FR] NOUVEAU PROCÉDÉ ET NOUVEL INTERMÉDIAIRE POUR PRÉPARATION D'ULIPRISTAL
  申请人：LUPIN LTD

  公开号：WO2014060888A1

  公开（公告）日：2014-04-24

  The present invention is related to a novel process for the preparation of ulipristal (I) that comprises reaction of 17-α-ethynyl-17-β-hydroxy-11-β-(4-N,N-dimethylamino phenyl)- 9-norpregna-4,9-diene-3-one (III) with phenyl sulphenyl chloride (IVa) or p-nitro phenyl sulphenyl chloride (IVb) in the presence of organic base and solvent to give sulfoxide (Va) or (Vb) respectively. Sulfoxides (Va) or (Vb) are reacted with alkali metal alkoxide in alcoholic solvent followed by treatment with aqueous acid. The present invention also relates to novel intermediate 11-β-(4-N,N-dimethylaminophenyl)-21(p- nitro-phenyl-sulphinyl)-19-norpregna-4(5), 9(10), 17(20) 20-tetraene, 3-one (Vb).

  本发明涉及一种用于制备尤利普利斯塔尔（I）的新型工艺，该工艺包括将17-α-乙炔基-17-β-羟基-11-β-(4-N，N-二甲胺基苯基)-9-诺孕烯-4,9-二烯-3-酮（III）与苯基亚砜氯化物（IVa）或对硝基苯基亚砜氯化物（IVb）在有机碱和溶剂存在下反应，分别得到亚砜氧化物（Va）或（Vb）。亚砜氧化物（Va）或（Vb）与醇性溶剂中的碱金属烷氧化物反应，随后经过水酸处理。本发明还涉及新型中间体11-β-(4-N，N-二甲基氨基苯基)-21(对硝基苯基亚砜基)-19-诺孕烯-4(5)，9(10)，17(20) 20-四烯-3-酮（Vb）。
• NOVEL PROCESS AND INTERMEDIATE FOR PREPARATION OF ULIPRISTAL
  申请人：LUPIN LIMITED

  公开号：US20150274770A1

  公开（公告）日：2015-10-01

  The present invention is related to a novel process for the preparation of ulipristal (I) that comprises reaction of 17-α-ethynyl-17-β-hydroxy-11-β-(4-N,N-dimethylamino phenyl)- 9-norpregna-4,9-diene-3-one (III) with phenyl sulphenyl chloride (IVa) or p-nitro phenyl sulphenyl chloride (Nb) in the presence of organic base and solvent to give sulfoxide (Va) or (Vb) respectively. Sulfoxides (Va) or (Vb) are reacted with alkali metal alkoxide in alcoholic solvent followed by treatment with aqueous acid. The present invention also relates to novel intermediate 11-β-(4-N,N-dimethylaminophenyl)-21(p- nitro-phenyl-sulphinyl)-19-norpregna-4(5), 9(10), 17(20) 20-tetraene, 3-one (Vb).

  本发明涉及一种新的制备ulipristal (I)的方法，其中包括将17-α-乙炔基-17-β-羟基-11-β-(4-N,N-二甲基氨基苯基)-9-去氢孕-4,9-二烯-3-酮(III)与苯基亚磺酰氯(IVa)或对硝基苯基亚磺酰氯(Nb)在有机碱和溶剂的存在下反应，分别得到亚砜(Va)或(Vb)。然后将亚砜(Va)或(Vb)与醇溶剂中的碱金属烷氧化物反应，随后用水酸处理。本发明还涉及新的中间体11-β-(4-N,N-二甲基氨基苯基)-21(p-硝基苯基亚磺酰基)-19-去氢孕-4(5),9(10),17(20)20-四烯-3-酮(Vb)。