7-methylcholesta-4,6-dien-3-one | 149280-70-6

• 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: 7-methylcholesta-4,6-dien-3-one
• 英文别名: 7-Methyl-Cholest-4,6-Dien-3-one；(8S,9S,10R,13R,14S,17R)-7,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 149280-70-6
• 化学式: C₂₈H₄₄O
• 分子量: 396.657
• InChiKey: JEZHPVIYLYQQFL-JBMPQMLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  7-methylcholesta-4,6-dien-3-one 在 氨 、 lithium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 7β-methyl-cholest-5-en-3-one
  参考文献：
  名称：

  A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol

  摘要：

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.

  DOI：

  10.1016/s0040-4039(00)60344-1
• 作为产物：
  描述：

  7-氧代胆甾-5-烯-3-beta-基乙酸酯 在 环己酮 、 aluminum isopropoxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 34.0h， 生成 7-methylcholesta-4,6-dien-3-one
  参考文献：
  名称：

  A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol

  摘要：

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.

  DOI：

  10.1016/s0040-4039(00)60344-1

文献信息

• Substituted 4-aza-5.alpha.-androstan-ones as 5.alpha.-reductase
  申请人：Merck & Co., Inc.

  公开号：US05693809A1

  公开（公告）日：1997-12-02

  Described are new 16-substituted and 7,16-disubstituted 4-aza-5.alpha.-androstan-3-ones and related compounds as 5.alpha.-reductase inhibitors.

  描述了新的16-取代和7,16-二取代的4-aza-5.alpha.-雄烷-3-酮及相关化合物，作为5.alpha.-还原酶抑制剂。
• 7.beta.-substituted-4-aza-5.alpha.-cholestan-3-ones as 5.alpha.
  申请人：Merck & Co., Inc.

  公开号：US05527807A1

  公开（公告）日：1996-06-18

  Described are new 7.beta.-substituted 4-aza-5.alpha.-cholestan-3-ones and related compounds as 5.alpha.-reductase inhibitors.

  介绍了新的7.beta.-取代的4-aza-5.alpha.-胆甾醇-3-酮及相关化合物作为5.alpha.-还原酶抑制剂。
• Combination method of treating acne using 4-AZA-5.alpha.-cholestan-ones
  申请人：Merck & Co., Inc.

  公开号：US05543417A1

  公开（公告）日：1996-08-06

  Described is a combination method using selective inhibitors of 5.alpha.-reductase 1 and/or 2 including 7.beta.-substituted 4-aza-5.alpha.-cholestan-3-ones and related 4-aza-5.alpha.-androstan-3-one compounds which are useful in the treatment of acne vulgaris in combination with at least one agent selected from an antibacterial, keratolytic, and/or an anti-inflammatory.

  描述了一种使用选择性5α-还原酶1和/或2的抑制剂的组合方法，包括7β-取代的4-氮杂-5α-胆甾-3-酮和相关的4-氮杂-5α-雄甾-3-酮化合物，这些化合物与至少一种从抗菌、角质溶解和/或抗炎药物中选择的药物组合在一起，用于治疗痤疮。
• New 7B-substituted-4-aza-5a-cholestan-ones as 5a-reductase inhibitors
  申请人：MERCK & CO. INC.

  公开号：EP0572165A1

  公开（公告）日：1993-12-01

  Described are new 7β-substituted 4-aza-5α-cholestan-3-ones and related compounds as 5α-reductase inhibitors.

  描述了作为 5α 还原酶抑制剂的新型 7β 取代 4-氮杂-5α-胆甾烷-3-酮及相关化合物。
• [EN] 7 beta -SUBSTITUTED-4-AZA-5 alpha -CHOLESTAN-3-ONES AS SELECTIVE 5 alpha -REDUCTASE 1 INHIBITORS<br/>[FR] 7 beta -SUBSTITUES-4-AZA-5 alpha -CHOLESTAN-3-ONES UTILISES COMME INHIBITEURS SELECTIFS DE LA 5 alpha -REDUCTASE 1
  申请人：MERCK & CO., INC.

  公开号：WO1995013077A1

  公开（公告）日：1995-05-18

  (EN) 7$g(b)-substituted 4-aza-5$g(a)-cholestan-3-ones and related compounds are selective inhibitors of 5$g(a)-reductase 1 useful in the treatment hyperandrogenic conditions.(FR) Les 7$g(b)-substitués-4-aza-5$g(a)-cholestan-3-ones et les composés apparentés sont des inhibiteurs sélectifs de la 5$g(a)-réductase 1 qui sont utiles dans le traitement des pathologies hyperandrogéniques.

  这些7$g(b)-取代基-4-aza-5$g(a)-cholestan-3-ones以及相关化合物是一类选择性抑制5$g(a)- reducease 1的药物，它们在治疗雄性激素过多的相关疾病中具有一定的应用价值。