21-Methoxypregna-1,4-diene-3,11,20-trione | 129786-21-6

• 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: 21-Methoxypregna-1,4-diene-3,11,20-trione
• 英文别名: (8S,9S,10R,13S,14S,17S)-17-(2-methoxyacetyl)-10,13-dimethyl-7,8,9,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,11-dione
• CAS: 129786-21-6
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: AYYLZFOMZFBUFJ-KVTLELNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  21-Methoxypregna-1,4-diene-3,11,20-trione 在 甲醇 、 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以51%的产率得到孕甾-1,4-二烯-3,11,20-三酮
  参考文献：
  名称：

  Efficient C-21 deoxygenation of 21-alkoxy-20-keto corticoid steroids with trimethylsilyl iodide in the presence of methanol

  摘要：

  Reaction of 21-alkyl ethers 1, 4-6, 8, and 9 with a large excess of trimethylsilyl iodide (TMSI) produced the deoxygenated products 3 and 11 in low to moderate yields along with a small amount of 21-alcohols 2 and 10. The deoxygenation reaction in the presence of 1.5 molar equiv of MeOH gave the products in much higher yields than those without MeOH, except the reaction of the ethyl and n-propyl ethers 4 and 5. Treatment of 1 and 8 with trimethylsilyl chloride/NaI in the presence of MeOH gave similar results to those with TMSI. Compound 3 was also produced in high yields by reaction of 1 and 4 with HI under mild conditions. On the other hand, treatment of 17-alpha-ketol 7 with TMSI in the presence of MeOH yielded 17-alpha-beta-methyl D-homo steroid 15. The results along with deuterium-labeling experiments with MeOD and IR and H-1 NMR spectral analysis during the reaction with TMSI suggest that dealkylation of the 21-alkyl ethers precedes the deoxygenation, in which HI produced in situ by reaction of MeOH with TMSI would be involved.

  DOI：

  10.1021/jo00001a062
• 作为产物：
  描述：

  21-hydroxy-1,4-pregnadiene-3,11,20-trione 、 碘甲烷 在 silver(l) oxide 作用下， 反应 11.0h， 以65%的产率得到21-Methoxypregna-1,4-diene-3,11,20-trione
  参考文献：
  名称：

  Efficient C-21 deoxygenation of 21-alkoxy-20-keto corticoid steroids with trimethylsilyl iodide in the presence of methanol

  摘要：

  Reaction of 21-alkyl ethers 1, 4-6, 8, and 9 with a large excess of trimethylsilyl iodide (TMSI) produced the deoxygenated products 3 and 11 in low to moderate yields along with a small amount of 21-alcohols 2 and 10. The deoxygenation reaction in the presence of 1.5 molar equiv of MeOH gave the products in much higher yields than those without MeOH, except the reaction of the ethyl and n-propyl ethers 4 and 5. Treatment of 1 and 8 with trimethylsilyl chloride/NaI in the presence of MeOH gave similar results to those with TMSI. Compound 3 was also produced in high yields by reaction of 1 and 4 with HI under mild conditions. On the other hand, treatment of 17-alpha-ketol 7 with TMSI in the presence of MeOH yielded 17-alpha-beta-methyl D-homo steroid 15. The results along with deuterium-labeling experiments with MeOD and IR and H-1 NMR spectral analysis during the reaction with TMSI suggest that dealkylation of the 21-alkyl ethers precedes the deoxygenation, in which HI produced in situ by reaction of MeOH with TMSI would be involved.

  DOI：

  10.1021/jo00001a062

文献信息

• NAGAOKA, MASAO;KUNITAMA, YURIE;NUMAZAWA, MITSUTERU, J. ORG. CHEM., 56,(1991) N, C. 334-338
  作者：NAGAOKA, MASAO、KUNITAMA, YURIE、NUMAZAWA, MITSUTERU

  DOI：——

  日期：——