(8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-methylaminomethyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol | 69269-28-9

• 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
• 英文名称: (8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-methylaminomethyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• 英文别名: (8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-17-(methylaminomethyl)-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 69269-28-9
• 化学式: C₂₂H₃₅NO₂
• 分子量: 345.525
• InChiKey: STJBYJSYYCBNKM-LXHROKJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-methylaminomethyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 (5S,8'R,9'S,13'S,14'S)-13'-ethyl-3'-methoxy-3-methylspiro[1,3-oxazolidine-5,17'-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-2-one
  参考文献：
  名称：

  Synthesis of new spiro-steroids, II: Steroid-17-spiro-oxazolidinones*1

  摘要：

  New, potential aldosterone blocking 17-spiro-oxazolidinone derivatives with androstane, estrane and 13 beta-ethyl-gonane ring system were synthesized. 17S-Spiro-oxiranes were used as starting compounds and the oxazolidinone ring was built up in different ways. All compounds but one were devoid of considerable endocrine activities. 3-Oxo-13 beta-ethyl-gona-4,9(10),11-triene-17S-spiro-5'-(2'-oxo-3'-methyl)oxazolidine shows significant antiandrogen activity on s.c., but none on p.o. administration.

  DOI：

  10.1016/0039-128x(80)90138-5
• 作为产物：
  描述：

  13β-ethyl-3-methoxy-gona-2,5(10)-diene-17S-spiro-oxirane 、 甲胺 在 对甲苯磺酸 作用下， 生成 (8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-methylaminomethyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Synthesis of new spiro-steroids, II: Steroid-17-spiro-oxazolidinones*1

  摘要：

  New, potential aldosterone blocking 17-spiro-oxazolidinone derivatives with androstane, estrane and 13 beta-ethyl-gonane ring system were synthesized. 17S-Spiro-oxiranes were used as starting compounds and the oxazolidinone ring was built up in different ways. All compounds but one were devoid of considerable endocrine activities. 3-Oxo-13 beta-ethyl-gona-4,9(10),11-triene-17S-spiro-5'-(2'-oxo-3'-methyl)oxazolidine shows significant antiandrogen activity on s.c., but none on p.o. administration.

  DOI：

  10.1016/0039-128x(80)90138-5

文献信息

• Neue 17-Spirosteroide, III. Synthese von Steroid-17-spiro-5′-(1′,2′,3′-oxathiazolidin)-2′-oxiden
  作者：Sándor Sólyom、Katalin Szilágyi、Lajos Toldy

  DOI：10.1002/jlac.198319830613

  日期：1983.6.15

  Aus den 17β-Hydroxy-17α-Hydroxy-17α-(methylaminomethyl)steroiden 1 wurden mit Thionylchlorid, N-Sulfinylamiden 3 und N,N′-Sulfinyldiaminen 6 die Steroid-17-spiro-5′-(1′,2′,3′-oxathiazolidin)-2′-oxide 2, eine neue Klasse des 17-Spirosteroide, hergestellt. Die neuen Spiroverbindungen entstehen als diastereomere Gemische. Je nach dem verwendeten Typ des Ringschlußreagenzes wurden verschiedene Diasteromeren-Verhältnisse

  从17β-羟基-17α-羟基17α-（甲基氨基甲基）甾体1与亚硫酰氯，N-亚磺酰胺3和N，N'-亚磺酰二胺6混合，甾体17-spiro-5'-（1'，2 '，3'-oxathiazolidine）-2'-oxide 2，这是一类新的17-螺类固醇。新的螺环化合物以非对映异构体混合物的形式出现。根据所使用的闭环试剂的类型，发现了不同的非对映异构体比率。借助1 H-NMR光谱确定异构体的结构。
• US4180505A
  申请人：——

  公开号：US4180505A

  公开（公告）日：1979-12-25