7α-hydroxycholest-5-en-3β-yl 3-acetate | 19317-90-9

• 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: 7α-hydroxycholest-5-en-3β-yl 3-acetate
• 英文别名: cholest-5-ene-3β,7α-diol 3-monoacetate；7α-hydroxycholest-5-en-3β-yl acetate；3β-acetoxy-7α-hydroxycholest-5-ene；3β-acetoxy-5-cholesten-7α-ol；3β-acetoxycholest-5-en-7α-ol；3β-acetoxy-5-en-7α-ol；[(3S,7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 19317-90-9
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: QRSNTERZEKNKIZ-RFNSQPKESA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  525.9±43.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7α-hydroxycholest-5-en-3β-yl 3-acetate 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 7β-aminocholesterol
  参考文献：
  名称：

  Stereoselective Synthesis of 7α- and 7β-Aminocholesterol as Δ8-Δ7 Sterol Isomerase Inhibitors, with Fungicidal Activities towards Resistant Strains

  摘要：

  A mixture of epimeric 7alpha- and 7beta-aminocholesterol was shown to be a stronger inhibitor of yeast cell growth than morpholine inhibitors. In fact, this epimeric mixture inhibits Delta8-Delta7-sterol reductase. This epimeric mixture is fungicidal and active against Saccharomyces cerevisiae resistant strains. Therefore, 7alpha- and 7beta-aminocholesterol were selectively synthesized. According to in vitro bioassay studies on resistant strains such as Candida tropicalis [Amphotericin B resistant; minimum inhibitory concentration (MIC) of Amp B: 12.5 mug/mL], the MIC values for 7beta-aminocholesterol and 7alpha-aminocholesterol were found to be 0.8 mug/mL and 1.5 mug/ mL, respectively. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<4075::aid-ejoc4075>3.0.co;2-7
• 作为产物：
  描述：

  胆固醇醋酸酯 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 生成 7α-hydroxycholest-5-en-3β-yl 3-acetate
  参考文献：
  名称：

  Barton,D.H.R.; Bubb,W.A., Journal of the Chemical Society. Perkin transactions I, 1977, p. 916 - 923

  摘要：

  DOI：

文献信息

• Ramachandran plot on the web
  作者：S.S. Sheik、P. Sundararajan、A.S.Z. Hussain、K. Sekar

  DOI：10.1093/bioinformatics/18.11.1548

  日期：2002.11.1

  Summary: A graphics package has been developed to display the main chain torsion angles phi, psi (φ, Ψ); (Ramachandran angles) in a protein of known structure. In addition, the package calculates the Ramachandran angles at the central residue in the stretch of three amino acids having specified the flanking residue types. The package displays the Ramachandran angles along with a detailed analysis output. This software is incorporated with all the protein structures available in the Protein Databank.

  Availability: This package is available over the world wide web at http://144.16.71.146/rp/ or http://dicsoft1.physics.iisc.ernet.in/rp.

  Contact: [e-mail]

  * To whom correspondence should be addressed.

  † This work is dedicated to Late Professor G. N. Ramachandran.

  摘要：已开发了一个图形软件包，用于显示已知结构蛋白质中的主链扭转角 phi, psi (φ, Ψ)（Ramachandran角度）。此外，该软件包计算了在具有指定侧链残基类型的三个氨基酸延伸中心残基处的Ramachandran角度。该软件包显示Ramachandran角度以及详细的分析输出。该软件已与蛋白质数据库中所有可用的蛋白质结构整合。 可用性：该软件包可通过全球网络访问，网址为 http://144.16.71.146/rp/ 或 http://dicsoft1.physics.iisc.ernet.in/rp。 联系方式：[e-mail] * 请将信函寄至。 † 本工作献给已故教授G. N. Ramachandran。
• MnO₂/TBHP: A Versatile and User-­Friend­ly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups
  作者：Stefano Serra

  DOI：10.1002/ejoc.201500829

  日期：2015.9

  activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased

  在活化的 MnO2 存在下，CH2Cl2 中的叔丁基过氧化氢 (TBHP) 能够氧化不同类别化合物的烯丙基和苄基亚甲基。我描述了基于两个连续步骤的一锅氧化方案。在低温下进行的第一步中，MnO2 催化亚甲基的氧化。这之后是第二步，其中反应温度升高，使 MnO2 既可以催化未反应的 TBHP 分解，又可以氧化可能形成的烯丙醇。所提出的氧化程序通常适用，尽管其效率、区域选择性和化学选择性在很大程度上取决于底物的结构。
• Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption
  作者：Samuel D. Offei、Hadi D. Arman、Francis K. Yoshimoto

  DOI：10.1016/j.steroids.2019.108449

  日期：2019.11

  syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature

  7α-Hydroxy-cholest-4-en-3-one是胆汁酸流失，肠易激综合征和其他与胆汁酸生物合成缺陷有关的疾病的生物标志物。此外，7α-羟基胆甾醇4-en-3-one是细胞色素P450 8B1（P450 8B1或CYP8B1）的生理底物，P450 8B1或CYP8B1是与肥胖症和心血管健康有关的氧固醇12α-羟化酶。我们从胆固醇开始报告了这种具有重要生理意义的氧固醇的化学合成。该合成的关键特征涉及3-脱氧-Δ4-7α-甲酸酯类固醇前体的区域选择性C3-烯丙基氧化形成7α-甲氧基-胆甾醇4-en-3-one，将其皂化生成7α-羟基-cholest-4-en-3-one。
• An improved synthesis of 1α-hydroxy Vitamin D3
  作者：W. Nerinckx、P.J. De Clercq、C. Couwenhoven、W.R.M. Overbeek、S.J. Halkes

  DOI：10.1016/s0040-4020(01)80888-7

  日期：1991.11

  described starting from the known previtamin D3 adduct 6. The sequence involves the stereoselective allylic bromination to 9, followed by substitution with mercuric(II)acetate which occurs with retention of configuration to yield acetate 22. Basic hydrolysis gives diol 7, a known precursor of 1α-OH vitamin D3.

  从已知的维生素原D 3加合物6开始描述了维生素D 3中1α-OH功能的高效立体选择引入。该序列包括将立体选择性的烯丙基溴化至9，然后用乙酸汞（II）取代，后者在保留构型的情况下发生，从而生成乙酸22。碱性水解得到已知的1α-OH维生素D 3的前体二醇7。
• Stereoselective 7.ALPHA.-Hydroxylation of 3.BETA.-Acetoxy-.DELTA.5-steroids by Fe(PA)3/H2O2/MeCN.
  作者：Eiichi KOTANI、Tetsuya TAKEYA、Hirotaka EGAWA、Seisho TOBINAGA

  DOI：10.1248/cpb.45.750

  日期：——

  Stereoselective 7α-hydroxylation reaction of Δ5-steroids by a Fe(PA; picolinate)3/H2O2/MeCN system is presented. The 7α-hydroxylation reactions were achieved in 33-40% yields by addition of 30%-H2O2 to a solution of 3β-acetoxy-Δ5-steroids 1a-1d and a crystalline of Fe(PA)3 in MeCN.

  通过Fe(PA; 皮考林酸盐)3/H2O2/MeCN体系实现了Δ5类固醇的立体选择性7α-羟基化反应。通过将30%-H2O2添加到含有3β-乙酰氧基-Δ5类固醇1a-1d和Fe(PA)3的MeCN溶液中，该反应的产率达到了33-40%。