7,15,16,17-tetrahydro-3-methoxy-17,17-dimethyl-6H-cyclopenta[ a]phenanthrene | 21691-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7,15,16,17-tetrahydro-3-methoxy-17,17-dimethyl-6H-cyclopenta[ a]phenanthrene
• 英文别名: 7,15,16,17-tetrahydro-3-methoxy-17,17-dimethyl-6H-cyclopenta[a]phenanthrene；3',3'-Dimethyl-7-methoxy-1,2-cyclopenteno-9,10-dihydro-phenanthrene；3-Methoxy-17.17-dimethyl-gonahexaen-(1.3.5(10).8.11.13)；3-methoxy-17,17-dimethyl-6,7,15,16-tetrahydrocyclopenta[a]phenanthrene
• CAS: 21691-95-2
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: AZYMWVZVIDXLGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,15,16,17-tetrahydro-3-methoxy-17,17-dimethyl-6H-cyclopenta[ a]phenanthrene 在 吡啶盐酸盐 作用下， 以 正己烷 、 水 为溶剂， 生成 7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  2,2-Dimethyl-2-[(7,15

  摘要：

  本发明公开了2,2-二甲基-2-[(7,15,16,17-四氢-17,17-二甲基-6H-环戊[a]菲-3-基)氧基]乙基脂肪二酸酯及其中间体的制备方法和降低高胆固醇作用。

  公开号：

  US04008257A1
• 作为产物：
  描述：

  3-甲氧基雌酮 在 盐酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 生成 7,15,16,17-tetrahydro-3-methoxy-17,17-dimethyl-6H-cyclopenta[ a]phenanthrene
  参考文献：
  名称：

  Torreilles; Crastes de Paulet, Bulletin de la Societe Chimique de France, 1968, vol. 12, p. 4886 - 4892

  摘要：

  DOI：

文献信息

• 2,2-Dimethyl-2-[(7,15
  申请人：G. D. Searle & Co.

  公开号：US04008257A1

  公开（公告）日：1977-02-15

  Preparation and the antihypercholesterolemic activity of 2,2-dimethyl-2-[(7,15,16,17-tetrahydro-17,17-dimethyl-6H-cyclopenta[a]phen anthren-3-yl)oxy]ethyl alkanedioates and intermediates thereto are disclosed.

  本发明公开了2,2-二甲基-2-[(7,15,16,17-四氢-17,17-二甲基-6H-环戊[a]菲-3-基)氧基]乙基脂肪二酸酯及其中间体的制备方法和降低高胆固醇作用。
• Chromogenic reactions of steroids with strong acids. IX. Behavior of estrone methyl ether in concentrated sulfuric acid.
  作者：TOSHIAKI MIURA、MICHIYA KIMURA

  DOI：10.1248/cpb.26.171

  日期：——

  The behavior of estrone methyl ether (V) in strong acid was studied, in order to elucidate the mechanism of the Kober color reaction. When V was dissolved into concentrated sulfuric acid, a maximum absorption gradually appeared at 465 nm which was then transferred to 452 nm with elapse of time. On the other hand, 3-methoxy-17α-methylestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIb) immediately gave the chromophoric cation χ-465 (VIIb) in concentrated sulfuric acid. Similarly, 3-methoxyestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIa) gave the cation χ-364 (XIVa) which changed in turn to χ-465 (VIIa). Sulfonation gradually occurred at C (2)s of VIIa and VIIb in the same acid to give the corresponding cations XIXa and XIXb ; the maximum absorption at 465 nm altered to 452 nm. The mechanism of the conversion of V into the C (2)-sulfonated χ-465 (XIXa) was elucidated from these behavior of XIIIa and XIIIb in concentrated sulfuric acid.

  研究了雌酮甲醚(V)在强酸中的行为，以阐明Kober显色反应的机理。当V溶解到浓硫酸中时，在465 nm处逐渐出现最大吸收，然后随着时间的推移转移到452 nm。另一方面，3-methoxy-17α-methylestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIb) 在浓硫酸中立即产生发色阳离子 χ-465 (VIIb) 。类似地，3-methoxyestra-1, 3, 5 (10), 9 (11)-tetraen-17β-ol (XIIIa) 得到阳离子 χ-364 (XIVa)，其又变为 χ-465 (VIIa)。在相同的酸中，VIIa和VIIb的C(2)处逐渐发生磺化，得到相应的阳离子XIXa和XIXb； 465 nm 处的最大吸收变为 452 nm。从XIIIa和XIIIb在浓硫酸中的这些行为阐明了V转化成C(2)-磺化χ-465(XIXa)的机制。
• US4008257A
  申请人：——

  公开号：US4008257A

  公开（公告）日：1977-02-15
• Torreilles; Crastes de Paulet, Bulletin de la Societe Chimique de France, 1968, vol. 12, p. 4886 - 4892
  作者：Torreilles、Crastes de Paulet

  DOI：——

  日期：——
• Potential hypolipidemic agents derived from 3-hydroxy-17,17-dimethylgona-1,3,5(10),8,11,13-hexaene
  作者：Leland J. Chinn、Karlene W. Salamon

  DOI：10.1021/jm00212a008

  日期：1977.2

  Numerous aryloxy derivatives containing a lipophilic group have been found to possess hypolipidemic activity. This has prompted the preparation of various derivatives of 3-hydroxy-17,17-dimethylgona-1,3,5(10),8,11,13-hexaene (6a). In 6a the lipophilic biphenyl group is incorporated into the steroid nucleus. A three-step synthesis of 6a from 17beta-methylestradiol methyl ether was developed. The derivatives prepared were tested in rats made hypercholesterolemic with propylthiouracil. Several were found active in this test.