Methyl 17α-Hydroxy-3,11-dioxoandrost-4-ene-17β-carboxylate | 3941-62-6

• 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: Methyl 17α-Hydroxy-3,11-dioxoandrost-4-ene-17β-carboxylate
• 英文别名: methyl 3,11-dioxo-17α-hydroxyandrost-4-ene-17-carboxylate；17-hydroxy-3,11-dioxo-androst-4-ene-17β-carboxylic acid methyl ester；17-Hydroxy-3,11-dioxo-androst-4-en-17β-carbonsaeure-methylester；17α-Hydroxy-Δ⁴-3,11-dion-aetiansaeure-methylester；methyl (8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-17-carboxylate
• CAS: 3941-62-6
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: JKXUNECVJIDEKM-PLBZXJNASA-N

物化性质

• 熔点：
  224-227 °C
• 沸点：
  502.8±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl 17α-Hydroxy-3,11-dioxoandrost-4-ene-17β-carboxylate 在 camphor-10-sulfonic acid 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 21.25h， 生成 17α-Hydroxy-17β-<<(S)-α-methoxy-α-(trifluoromethyl)phenylacetoxy>methyl>androst-4-ene-3,11-dione
  参考文献：
  名称：

  First enantioselective total synthesis of (+)-cortisone

  摘要：

  DOI：

  10.1021/jo00308a022
• 作为产物：
  描述：

  3,11-dioxo-17α-hydroxyandrost-4-ene-17-carbonitrile 在 盐酸 作用下， 以95%的产率得到Methyl 17α-Hydroxy-3,11-dioxoandrost-4-ene-17β-carboxylate
  参考文献：
  名称：

  Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2', 4' -diones from 17-keto steroids

  摘要：

  Spiro[androst-4-en-17alpha, 5'-oxazolidine]-2', 3, 4'-trione 8-alpha and spiro]androst-4-en-17alpha, 5'-oxazolidine[-2', 3, 4', 11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkychlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid 17-alpha-hydroxy-17-carboxyesters and 17-alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.

  DOI：

  10.1016/0039-128x(90)90088-s

文献信息

• The transformation of d-homosteroids to steroids
  作者：V. Georgian、N. Kundu

  DOI：10.1016/s0040-4020(01)99358-5

  日期：1963.1

  toward transforming the products so obtained to d-homo-17,17a-diones. The latter, conveniently prepared by this means, were studied in the benzilic acid rearrangement mode of ring contraction back to steroids bearing a 17β-carboxyl and a 17β-hydroxyl. This rearrangement has been found to proceed in one steric sense, which may be accounted for on the basis of intermediates generated in compliance with the

  为了将如此获得的产物转化为d-homo-17，17a-二酮，已经实现了某些皮质激素的d-同型环化。后者通过这种方法方便地制备，以苯环酸重排模式将环收缩回到带有17β-羧基和17β-羟基的甾族化合物上进行了研究。已经发现这种重排是在一种空间意义上进行的，这可以根据按照构象分析原理产生的中间体来解释。
• NEMOTO, HIDEO;MATSUHASHI, NORIKAZU;IMAIZUMI, MARI;NAGAI, MITSUO;FUKUMOTO,+, J. ORG. CHEM., 55,(1990) N1, C. 5625-5631
  作者：NEMOTO, HIDEO、MATSUHASHI, NORIKAZU、IMAIZUMI, MARI、NAGAI, MITSUO、FUKUMOTO,+

  DOI：——

  日期：——
• Reich et al., Journal of Biological Chemistry, 1950, vol. 187, p. 411,416
  作者：Reich et al.

  DOI：——

  日期：——