5α-pregn-1-en-3-one | 23925-79-3

• 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: 5α-pregn-1-en-3-one
• 英文别名: (5S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 23925-79-3
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: HPEXCOZMEGKVLT-PMJYHDSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5α-pregnan-3β-ol 在 pyridinium chlorochromate 、 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 17.0h， 生成 5α-pregn-1-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

文献信息

• 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.