5β-pregnan-3-one | 1474-66-4

• 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: 5β-pregnan-3-one
• 英文别名: 5β-Pregnan-3-on；5β-Pregnanon-(3)；5beta-Pregnane-3-one；(5R,8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1474-66-4
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: JMAPHBFIBIHSIT-XEDOOJRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5β-pregnan-3-one 在 三氟乙酸 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以42%的产率得到pregn-4-en-3-one
  参考文献：
  名称：

  Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis

  摘要：

  Mild and regioselective conversion of 3-keto-5 alpha- and 3-keto-5 beta-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Delta(1)- and Delta(4)-3-ketones) by treatment with oiodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the alpha- and beta-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.11.007
• 作为产物：
  描述：

  孕烷醇酮 在 chromium(VI) oxide 、 盐酸 、 amalgamated zinc 、 溶剂黄146 作用下， 生成 5β-pregnan-3-one
  参考文献：
  名称：

  Sterols. XLIV. Pregnanone-3 and Related Compounds^*

  摘要：

  DOI：

  10.1021/ja01277a040

文献信息

• Sterols. LI. Δ⁴-Pregnenone-3
  作者：Russell E. Marker、Elmer J. Lawson

  DOI：10.1021/ja01872a014

  日期：1939.3
• Haworth et al., Journal of the Chemical Society, 1956, p. 3749,3751
  作者：Haworth et al.

  DOI：——

  日期：——
• Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis
  作者：Takashi Iida、Kaoru Omura、Ryou Sakiyama、Mitsuo Kodomari

  DOI：10.1016/j.chemphyslip.2013.11.007

  日期：2014.2

  Mild and regioselective conversion of 3-keto-5 alpha- and 3-keto-5 beta-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Delta(1)- and Delta(4)-3-ketones) by treatment with oiodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the alpha- and beta-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones. (C) 2013 Elsevier Ireland Ltd. All rights reserved.
• Sterols. XLIV. Pregnanone-3 and Related Compounds^*
  作者：Russell E. Marker、Elmer J. Lawson

  DOI：10.1021/ja01277a040

  日期：1938.10