4β,5-dihydroxy-5α-cholestane | 20233-47-0

• 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: 4β,5-dihydroxy-5α-cholestane
• 英文别名: 4β,5α-dihydroxycholestane；cholestane-4β,5α-diol；cholestan-4β,5α-diol；5α-cholestane-4β,5-diol；5α-Cholestan-4β,5-diol；(10R)-4c.5t-Dihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5alpha-Cholestane-4beta,5-diol；(4S,5S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-4,5-diol
• CAS: 20233-47-0
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: XHJMYRAEGCTDKQ-UEWDELQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4β,5-dihydroxy-5α-cholestane 在 吡啶 、 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 24.0h， 以90%的产率得到5-oxo-4,5-secocholestan-4-al
  参考文献：
  名称：

  Studies of the synthesis of biomarkers. XI. Synthesis of 4,5-secocholestane and 4-methyl-4,5-secocholestane

  摘要：

  4,5-Secocholestane (1a) and 4-methyl-4,5-secocholestane (1b) were synthesized from cholesterol (2) in five and seven steps, respectively. The key intermediate, 5-oxo-4,5-secocholestan-4-al (7) was reduced by the Clemmensen method to afford 1a. Meanwhile, 7 underwent selective Wittig reaction, Clemmensen reduction, and hydrogenation to give another target molecule, 1b. The structure of an unknown biomarker was shown to be different from the proposed 1a by gas chromatographic and mass spectrometric comparison.

  DOI：

  10.1016/0039-128x(92)90024-4
• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 1,4-二氧六环 、 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 四氧化锇 、 二乙二醇二乙醚 、 boron fluoride ether 、 双氧水 、 镍 、 溶剂黄146 作用下， 生成 4β,5-dihydroxy-5α-cholestane
  参考文献：
  名称：

  Characterization of the Products from Oxidation of Cholestenone with Osmium Tetroxide

  摘要：

  DOI：

  10.1021/ja01521a050

文献信息

• Hydroxy-steroids. Part XI. The preparation and infrared spectra of vicinal cholestanediols
  作者：C. W. Davey、E. L. McGinnis、J. M. McKeown (née Chancellor)、G. D. Meakins、M. W. Pemberton、R. N. Young

  DOI：10.1039/j39680002674

  日期：——

  Twenty-eight vicinal cholestanediols (positions 1,2; 2,3; 3,4; 4,5; 5,6; 6,7; and 7,8) have been prepared by unambiguous routes starting from the corresponding olefins. The O–H stretching bands of dilute solutions of these diols and of seven reference compounds have been examined under high dispersion. Characteristic differences between ax,ax, ax,eq, and eq,eq compounds were observed. It was concluded

  已经通过从相应的烯烃开始的明确途径制备了二十八个邻位胆固醇二醇（1,2,2,3; 3,4; 4,5; 5,6; 6,7和7,8位）。这些二醇和七种参考化合物的稀溶液的O–H伸缩带已在高分散度下进行了检测。观察到ax，ax，ax，eq和eq，eq化合物之间的特性差异。结论是，不能通过游离和键合羟基的吸收之间的频率差来获得羟基之间的二面角的精确值。
• Steroids and Walden inversion. Part LIX. Reactions of some steroid α-hydroxyamines
  作者：C. W. Shoppee、P. Ram、S. K. Roy

  DOI：10.1039/j39660001023

  日期：——

  Reduction of 5-hydroxy-5α-cholestan-4-one oxime and 5-hydroxy-5α-cholestan-6-one oxime with sodium–ethanol and lithium aluminium hydride gives, inter alia, the 4β-, 6α-, and 6β-amino-5-hydroxy-5α-cholestanes, whose deamination is described and briefly discussed. Attempts to dehydrate these α-hydroxy-amines to the related allylic amines were unsuccessful, as also were attempted ammonolyses of 4β-chlorocholest-5-ene

  用钠-乙醇和氢化铝锂还原5-羟基-5α-胆甾烷-4-一肟和5-羟基-5α-胆甾烷-6-一肟，除其他外，得到4β-，6α-和6β-氨基-5-羟基-5α-胆甾烷，其脱氨基作用已描述并作了简要讨论。将这些α-羟基胺脱水为相关的烯丙基胺的尝试均未成功，也尝试了4β-chlorocholest-5-ene和6β-chlorocholest-4-ene的氨解反应。
• The arabinofuranoside method, a convenient substitute of the fucofuranoside method for determining the absolute configuration of the secondary alcohols
  作者：Masaru Kobayashi

  DOI：10.1016/s0040-4020(02)01248-6

  日期：2002.11

  fucofuranoside method, a recently devised technique for determining the absolute configuration of secondary alcohols by 13C NMR, the arabinofuranoside method is proposed. Unlike fucose, the derivatizing agent arabinofuranose tetraacetate is available quantitatively by acid treatment of arabinose followed by acetylation. Application to the ten alcohols, previously tested for fucofuranoside method, showed essentially

  作为呋喃呋喃糖苷方法的简单替代品，提出了一种最近设计的通过13 C NMR测定仲醇的绝对构型的技术，即阿拉伯呋喃糖苷方法。与岩藻糖不同，阿拉伯糖呋喃糖四乙酸酯可通过酸处理阿拉伯糖然后进行乙酰化来定量获得。到10醇，先前针对fucofuranoside方法测试的应用程序，显示基本上相同的Δ δ Ç和Δ δ ħ值，表明D-阿拉伯呋喃糖苷方法是用于确定仲醇的绝对构型同样有用。
• REDUCTION OF PYRIDYL CARBINOLS WITH SODIUM BOROHYDRIDE/TRIFLUOROACETIC ACID
  作者：Charles F. Nutaitis、Thomas J. Greshock、Stephen R. Houghton、Lynn N. Moran、Melissa A. Walter

  DOI：10.1080/00304940209356774

  日期：2002.6

  the synthesis of diand triheteroarylmethanes from carbinols possessing thiophene, furan, benzothiophene, benzofuran, or phenyl substituents, and in 1997 to the reduction of 1,3-azole and 1,3-benzazole carbinols provided there was an additional aryl or pi-excessive heteroaryl (thienyl, benzo[b]thienyl, furyl, or benzo[b]furyl) substituent.3 Carbinols possessing a 1,3-azole or 1,3-benzazole ligand and

  1977 年，Gribble 和同事报告说，可以用硼氢化钠/三氟乙酸有效地还原二芳基甲醇和三芳基甲醇，得到相应的二芳基甲烷和三芳基甲烷。1991 年，Nutaitis 和同事 2 将这种方法扩展到从具有噻吩、呋喃、苯并噻吩、苯并呋喃或苯基取代基的甲醇合成二和三杂芳基甲烷，并在 1997 年减少了提供的 1,3-唑和 1,3-苯并唑甲醇有一个额外的芳基或π-过量杂芳基（噻吩基、苯并[b] 噻吩基、呋喃基或苯并[b]呋喃基）取代基。3 具有 1,3-唑或 1,3-苯并唑配体的甲醇和仅一个额外的芳基或杂芳基取代基对还原呈惰性。以此类推，预计具有吡啶基取代基取代 1,3-唑/l 的化合物，3-苯并唑配体的行为类似。这种转化将证明是有用的，因为相应的 α-取代的吡啶基甲烷已被证明是有价值的杀真菌剂、“肝微粒体血红素加氧酶和细胞色素 P450 的诱导剂”、多种金属的提取剂，包括铬、6”金?h 锌、和钴、6d
• The 13C NMR Method for Determining the Absolute Configuration of the 1,2-Glycols Consisting of Secondary and Tertiary Hydroxyl Groups
  作者：Masaru Kobayashi

  DOI：10.1016/s0040-4020(00)00070-3

  日期：2000.3

  13 C NMR method for determining the absolute configuration of secondary alcohols, is applied to five known steroids having a 1,2-glycol group composed of secondary and tertiary hydroxyl groups. The 1,2-alignment of the polar fucofuranosyl and tertiary hydroxyl group was found to have little influence on the requisite conformation of the glycosidic linkage. It showed the normal pattern of the distribution

  摘要 岩藻呋喃糖苷法是测定仲醇绝对构型的 13 C NMR 方法，适用于五种已知的具有由仲羟基和叔羟基组成的 1,2-二醇基团的甾体。发现极性岩藻呋喃糖基和叔羟基的 1,2-排列对糖苷键的必要构象几乎没有影响。它显示了 Δ δ C （和 Δ δ H ）值分布的正常模式，如先前对简单单羟基衍生物观察到的那样，证明了该方法对此类化合物的有用性。