4,4-dimethyl-5α-cholest-7-en-3β-ol | 6384-28-7

• 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: 4,4-dimethyl-5α-cholest-7-en-3β-ol
• 英文别名: 4,4-Dimethyl-5alpha-cholest-7-en-3beta-ol；(3S,5R,9R,10R,13R,14R,17R)-4,4,10,13-tetramethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 6384-28-7
• 化学式: C₂₉H₅₀O
• 分子量: 414.715
• InChiKey: UVNXFLZMQCAWCP-RCTKLBHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-5α-cholest-7-en-3β-ol 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 selenium(IV) oxide 、 硫酸 、 水 、 二异丁基氢化铝 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 47.5h， 生成 3β-hydroxylanost-7-en-32-al
  参考文献：
  名称：

  Regioselective synthesis of .DELTA.6-, .DELTA.7-, and .DELTA.8-14.alpha.-cyanosterol derivatives: versatile precursors to 14.alpha.-demethylase inhibitors

  摘要：

  The efficient preparation of 3-beta-(benzoyloxy)-4,4-dimethyl-5-alpha-cholest-8(14)-en-7-one (4a) and 3-beta-benyloxy)-5-alpha-ergost-8(14)-en-7-one (4b) and their conversion to DELTA-6-, DELTA-7- or DELTA-8-14-alpha-functionalized sterols is reported. The alkylaluminum-mediated 1,4-addition of HCN (Nagata reaction) to enones 4a,b is used to introduce the 14-alpha-substituent. Reduction of these conjugate addition products (5a,b) affords the 7-alpha-hydroxysterols (6a,b). The dehydration of 6a with Martin sulfurane reagent regioselectively produces the DELTA-6-14-alpha-cyanosterol 8. Alternatively, mesylation of 6a and elimination affords a mixture of DELTA-7:DELTA-6-sterols (3:1) from which the DELTA-6-sterol is removed by selective ozonolytic degradation. The ozonolytic stability of the DELTA-7-14-alpha-cyanosterols is also exploited in the preparation of 14-alpha-cyanosterols possessing modified side chains. Ozonolysis of 3-beta-(benzoyloxy)-5-alpha-ergost-7,22-diene-14-alpha-carbonitrile (9b) gave 18, which is used to prepare compounds containing the "24 methenyl" (21) and "lanosterol" (23) side chains. The trapping of the intermediate aluminum enolate formed in the hydrocyanation of 4a gives an 8-beta-bromosterol 13. Dehydrobromination of 13 provides a novel regioselective synthesis of the difficult to prepare DELTA-8-14-alpha-functionalized sterol 14.

  DOI：

  10.1021/jo00038a024
• 作为产物：
  描述：

  (3β,20R)-4,4-dimethylcholesta-5,7-dien-3-ol 生成 4,4-dimethyl-5α-cholest-7-en-3β-ol
  参考文献：
  名称：

  Lederer,F.; Ourisson,G., Bulletin de la Societe Chimique de France, 1965, p. 1295 - 1298

  摘要：

  DOI：

文献信息

• Steroidal 14.alpha.-carboxy-alkyl derivatives as regulators of HMG-COA
  申请人：SmithKline Beecham Corporation

  公开号：US05023250A1

  公开（公告）日：1991-06-11

  New 14.alpha.-carboxyalkyl sterols are regulators of HMG-CoA reductase and inhibitors of mammalian 14.alpha.-methyl demethylase and are useful in lowering serum cholesterol levels and treating fungal infections.

  新的14.alpha.-羧基烷基甾醇是HMG-CoA还原酶的调节剂和哺乳动物14.alpha.-甲基去甲基酶的抑制剂，可用于降低血清胆固醇水平和治疗真菌感染。
• The Role of Cytochrome b5in 4α-Methyl-Oxidation and C5(6) Desaturation of Plant Sterol Precursors
  作者：Alain Rahier、Mark Smith、Maryse Taton

  DOI：10.1006/bbrc.1997.6974

  日期：1997.7

  membrane-bound sterol-4alpha-methyl-oxidases and sterol C5(6)-desaturase of plant sterol biosynthesis have not been previously identified. The requirement of cytochrome b5 to shuttle reducing equivalents from NAD(P)H to 4,4-dimethylsterol-4alpha-methyl oxidase (4,4-DMSO), 4alpha-methylsterol-4alpha-methyl oxidase (4alpha-MSO), and delta7-sterol-C5(6) desaturase (5-DES) was investigated using a purified

  先前尚未确定植物固醇生物合成的膜结合固醇4α-甲基氧化酶和固醇C5（6）-去饱和酶的电子供体。要求细胞色素b5将还原当量从NAD（P）H转运至4,4-二甲基固醇-4α-甲基氧化酶（4,4-DMSO），4α-甲基固醇-4α-甲基氧化酶（4alpha-MSO）和delta7使用针对植物细胞色素b5产生的IgG纯化制剂，研究了-sterol-C5（6）去饱和酶（5-DES）。在玉米微粒体制剂中，抗体强烈而完全地抑制了4,4-DMSO，4alpha-MSO和5-DES的活性，这些活性不是由细胞色素P-450介导的，是三个氧化反应。另外，在相同的制剂中，IgG也抑制NADH依赖性细胞色素c的减少。
• Gautschi; Bloch, Journal of Biological Chemistry, 1958, vol. 233, p. 1343,1346
  作者：Gautschi、Bloch

  DOI：——

  日期：——
• Ohki,E., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 229 - 235
  作者：Ohki,E.

  DOI：——

  日期：——
• Brady D.R.; Crowder R.D.; Hayes W.J., J Biol Chem, 1980, 0021-9258, 10624-9
  作者：Brady D.R.、Crowder R.D.、Hayes W.J.

  DOI：——

  日期：——