3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate | 39933-10-3

• 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,5-dihydroxy-5α-androstane-6,17-dione 3-acetate
• 英文别名: 3β-acetoxy-5-hydroxy-5α-androstane-6,17-dione；5α-hydroxy-6,17-dioxoandrostane-3β-yl acetate；3β-acetoxy-5α-hydroxyandrostane-6,17-dione；androstane-3β,5α-diol-6,17-dione-3-acetate；3β-acetoxy-5α-hydroxyandrosten-6,17-dione；5-hydroxy-3β-acetoxy-5α-androstanedione-(6.17)；[(3S,5R,8R,9S,10R,13S,14S)-5-hydroxy-10,13-dimethyl-6,17-dioxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 39933-10-3
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: NMHSNRRBGTVQFD-SXWHVLJBSA-N

物化性质

• 熔点：
  196-198 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate 在 吡啶 、 氯化亚砜 、 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 生成 3-羟基雄甾-4-烯-6,17-二酮
  参考文献：
  名称：

  Labler,L. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2226 - 2237

  摘要：

  DOI：
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 chromium(VI) oxide 、 己二酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 丁酮 、 苯 为溶剂， 反应 28.0h， 生成 3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO
  作者：Marco Frigerio、Marco Santagostino

  DOI：10.1016/0040-4039(94)80038-3

  日期：1994.10

  o-Iodoxybenzoic acid (IBX) smoothly oxidizes primary and secondary alcohols to aldehydes and ketones, respectively. 1,2-Diols are converted to α-ketols or α-diketones without any oxidative cleavage of the glycol CC bond. IBX oxidations are easily conducted in DMSO solution at room temperature, with yields ranging from good to quantitative.

  邻碘氧苯甲酸（IBX）分别将伯醇和仲醇平滑氧化为醛和酮。1,2-二醇可转化为α-酮醇或α-二酮，而乙二醇CC键没有任何氧化裂解。IBX氧化很容易在室温下的DMSO溶液中进行，收率范围从良好到定量。
• Tin(<scp>II</scp>) chloride dihydrate–a mild reagent for the transformation of 6-nitro-Δ⁵-steroids to 5α-hydroxy-6-ketosteroids
  作者：Gireesh M. Singhal、Nalin B. Das、Ram P. Sharma

  DOI：10.1039/c39900000498

  日期：——

  Reaction of excess hydrated tin(II) chloride with 6-nitro-Δ5-steroids (1a–g) and (5) in tetrahydrofuran furnishes 5α-hydroxy-6-ketosteroids (2a–g) and (6) respectively, in good yields.

  过量水合氯化亚锡与6-硝基-Δ5-甾体（1a-g）及（5）在四氢呋喃中的反应，分别以良好产率得到5α-羟基-6-酮甾体（2a-g）及（6）。
• Szczepek, Wojciech, Acta Chimica Hungarica, 1986, vol. 123, # 3-4, p. 69 - 76
  作者：Szczepek, Wojciech

  DOI：——

  日期：——
• Dawidar, A. M.; Saleh, A. A.; Abdel-Malek, M. M., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 1, p. 102 - 106
  作者：Dawidar, A. M.、Saleh, A. A.、Abdel-Malek, M. M.

  DOI：——

  日期：——
• INVESTIGATIONS ON STEROIDS. III. PARTIAL OXIDATION OF 3,5,6-TRIOLS AND OXIDATION WITH PERMANGANATE OF 5,6-UNSATURATED STEROIDS¹
  作者：MAXIMILIAN EHRENSTEIN、MARGUERITE TWADDELL DECKER

  DOI：10.1021/jo01211a007

  日期：1940.9