3β,7α-cholest-5-ene-3,7-diol-3-benzoate | 40824-59-7

• 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: 3β,7α-cholest-5-ene-3,7-diol-3-benzoate
• 英文别名: cholest-5-ene-3β,7α-diol 3-benzoate；7α-Hydroxy-cholesteryl-benzoat；3β-benzoyloxy-cholest-5-en-7α-ol；Benzoesaeure-(7α-hydroxy-cholesten-(5)-yl-(3β)-ester)；(3b,7a)-Cholest-5-ene-3,7-diol 3-Benzoate；[(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] benzoate
• CAS: 40824-59-7
• 化学式: C₃₄H₅₀O₃
• 分子量: 506.769
• InChiKey: YAQOZGBTTMUPRW-KHCFEYDLSA-N

物化性质

• 熔点：
  160.5-161.5°C
• 沸点：
  595.0±43.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  3β,7α-cholest-5-ene-3,7-diol-3-benzoate 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 生成 胆甾-5-烯-3,7二醇
  参考文献：
  名称：

  A convenient synthesis of 7α-hydroxycholest-4-en-3-one by the hydroxypropyl-β-cyclodextrin-facilitated cholesterol oxidase oxidation of 3β,7α-cholest-5-ene-3,7-diol

  摘要：

  The initial biosynthetic conversions of cholesterol to the bile acids involve sequential 7 alpha-hydroxylation (catalyzed by cholesterol 7 alpha-hydroxylase) followed by C-3 oxidation and concomittant double bond migration (to a Delta(4)-configuration, catalyzed by 3 beta-Delta(5)-C-27-steroid oxidoreductase) to provide 7 alpha-hydroxycholest-4-en-3-one. A straightforward, and economical, preparation (on a 0.1 g scale) of this pivotal biosynthetic intermediate has been devised. Reduction of 3 beta-(benzoyloxy)-cholest-5-en-7-one with LiB(sec-butyl)(3)H provided a 4:1 mixture, respectively, of the 7 alpha- and 7 beta-hydroxy diastereomers, which were separated chromatographically. Solvolytic removal of the C-3 benzoyl group gave 3 beta,7 alpha-cholest-5-ene-3,7-diol. A suspension of the 1:1 (nu/nu) complex (formed by mutual dissolution in MeOH, followed by evaporation of the solvent) of this diol with hydroxypropyl-beta-cyclodextrin, at a concentration of 1 mg mL(-1) (in neutral phosphate bl(buffer), was converted by Brevibacterium sp cholesterol oxidase (0.25 U mg(-1) of substrate) and catalase (70 U mg(-1) of substrate, to recover O-2 from the H2O2 produced by the enzymatic oxidation) to a suspension of 7 alpha-hydroxycholest-4-en-3-one and the hydroxypropyl-beta-cyclodextrin. The yield for the enzymatic conversion was in excess of 90%. A much poorer and less reproducible yield (<20%) was seen in the absence of the hydroxypropyl-beta-cyclodextrin. Routine extraction of this aqueous suspension, and chromatographic purification (85:15 CHCl3/acetone nu/nu on silica) of the residue, gave pure 7 alpha-hydroxycholest-4-en-3-one in 68% isolated yield. This route is a significant improvement, in terms of reaction scale and convenience, over the previous procedures for the preparation of this steroid.

  DOI：

  10.1016/0039-128x(95)93851-o
• 作为产物：
  描述：

  5-胆甾烯-3β-醇-7-酮 在 sodium hydroxide 、 双氧水 、 L-Selectride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3β,7α-cholest-5-ene-3,7-diol-3-benzoate
  参考文献：
  名称：

  A convenient synthesis of 7α-hydroxycholest-4-en-3-one by the hydroxypropyl-β-cyclodextrin-facilitated cholesterol oxidase oxidation of 3β,7α-cholest-5-ene-3,7-diol

  摘要：

  The initial biosynthetic conversions of cholesterol to the bile acids involve sequential 7 alpha-hydroxylation (catalyzed by cholesterol 7 alpha-hydroxylase) followed by C-3 oxidation and concomittant double bond migration (to a Delta(4)-configuration, catalyzed by 3 beta-Delta(5)-C-27-steroid oxidoreductase) to provide 7 alpha-hydroxycholest-4-en-3-one. A straightforward, and economical, preparation (on a 0.1 g scale) of this pivotal biosynthetic intermediate has been devised. Reduction of 3 beta-(benzoyloxy)-cholest-5-en-7-one with LiB(sec-butyl)(3)H provided a 4:1 mixture, respectively, of the 7 alpha- and 7 beta-hydroxy diastereomers, which were separated chromatographically. Solvolytic removal of the C-3 benzoyl group gave 3 beta,7 alpha-cholest-5-ene-3,7-diol. A suspension of the 1:1 (nu/nu) complex (formed by mutual dissolution in MeOH, followed by evaporation of the solvent) of this diol with hydroxypropyl-beta-cyclodextrin, at a concentration of 1 mg mL(-1) (in neutral phosphate bl(buffer), was converted by Brevibacterium sp cholesterol oxidase (0.25 U mg(-1) of substrate) and catalase (70 U mg(-1) of substrate, to recover O-2 from the H2O2 produced by the enzymatic oxidation) to a suspension of 7 alpha-hydroxycholest-4-en-3-one and the hydroxypropyl-beta-cyclodextrin. The yield for the enzymatic conversion was in excess of 90%. A much poorer and less reproducible yield (<20%) was seen in the absence of the hydroxypropyl-beta-cyclodextrin. Routine extraction of this aqueous suspension, and chromatographic purification (85:15 CHCl3/acetone nu/nu on silica) of the residue, gave pure 7 alpha-hydroxycholest-4-en-3-one in 68% isolated yield. This route is a significant improvement, in terms of reaction scale and convenience, over the previous procedures for the preparation of this steroid.

  DOI：

  10.1016/0039-128x(95)93851-o

文献信息

• Über die epimeren 7-Brom-cholesterylester und die Konfiguration der C-7-Substituenten in der Cholesterinreihe
  作者：H. Schaltegger、F. X. Müllner

  DOI：10.1002/hlca.19510340416

  日期：——

  vorliegen. Das 7α-Brom-cholesterylbenzoat ist das thermodynamisch labilere Epimere. Es wurden die Resultate mit analogen Fällen der Literatur verglichen. Aus der Übereinstimmung im chemischen und thermodynamischen Verhalten sowie der Übereinstimmung der molekularen Rotationsdifferenzen beim Vergleich mit anderen Steroiden mit Allylstruktur wurde mit Sicherheit geschlossen, dass in den positiv drehenden

  Es wurde gezeigt，Deurs bei der direkten Photobromierung von Cholesterinestern和bei der Bromierung mit Bromsuccinimid alsPrimärproduktenur7α-Brom-cholesterylesterentstehen，deren Struktur bewiesen wurde。在极化Lösungsmittelnzu einem Gleichgewicht中，死于beiden epimeren 7-溴-胆固醇胆固醇苯甲酸酯Epimerisieren，分别在70％7β-Brom-胆固醇胆固醇苯甲酸酯和30％7α-Brom-胆固醇胆固醇苯甲酸酯中。Das7α-溴-胆固醇基苯甲酸酯和热不稳定的Epimere。Es wurden die产生了Fällender Literatur
• 363. Studies in the sterol group. Part L. 7-substituted cholesterol derivatives and their stereochemistry (part III). 7-alkoxycholesterol derivatives
  作者：H. B. Henbest、E. R. H. Jones

  DOI：10.1039/jr9480001798

  日期：——
• ?-Cholestenon und epi-?-Cholestenon
  作者：W. Buser

  DOI：10.1002/hlca.19470300532

  日期：1947.8.1
• Stereospecific Syntheses of the 7-Deuterio- and 7-Tritiocholesterols. The Mechanism of Enzyme-catalyzed Hydroxylation at a Saturated Carbon Atom
  作者：E. J. Corey、George A. Gregoriou

  DOI：10.1021/ja01521a053

  日期：1959.6
• Bergmann; Meyers, Justus Liebigs Annalen der Chemie, 1959, vol. 620, p. 46,60
  作者：Bergmann、Meyers

  DOI：——

  日期：——