3α,4α-epoxy-5-cholesten-7-one | 22799-20-8

• 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: 3α,4α-epoxy-5-cholesten-7-one
• 英文别名: 3α,4α-epoxy-5-en-cholest-7-one；3α,4α-Epoxycholest-5-en-7-on；3a,4a-Epoxycholest-5-en-7-one；(1S,2R,5R,7S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-6-oxapentacyclo[9.7.0.02,8.05,7.012,16]octadec-8-en-10-one
• CAS: 22799-20-8
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: VBVKGEJMFZRMDE-KBUAHTBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3α,4α-epoxy-5-cholesten-7-one 在 氯化亚砜 、 氢溴酸 作用下， 以 吡啶 、 乙醚 、 氯仿 、 溶剂黄146 为溶剂， 反应 33.66h， 生成 5-cholestene-3β,7α,19-triol triacetate
  参考文献：
  名称：

  Stary, Ivo; Kocovsky, Pavel, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 5, p. 1227 - 1238

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇醋酸酯 在 盐酸 、 叔丁基过氧化氢 、 ruthenium(III) trichloride hydrate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 环己烷 、 水 为溶剂， 反应 11.0h， 生成 3α,4α-epoxy-5-cholesten-7-one
  参考文献：
  名称：

  Synthesis of steroidal and nonsteroidal vicinal heterocyclic alcohols, N-(1-cycloalkenyl)heterocycles and their antibacterial studies

  摘要：

  A solvent free steroidal and nonsteroidal epoxide ring opening reaction by nitrogen containing heterocycles under microwave irradiation is described. Some of the epoxide ring opening compounds were converted to their corresponding N-(1-cycloalkenyl)heterocycles via an acid catalyzed dehydration reaction. The antimicrobial activities of the epoxide ring opening compounds and N-(1-cycloalkenyl)heterocyclic compounds were tested by agar diffusion assay. Compounds 6, 9-12, 24 and 27 showed moderate inhibition against the growth of pathogenic bacteria Escherichia coli, Pseudomonas syringae, Bacillus subtilis, Proteus vulgaris and Staphylococcus aureus. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.03.011

文献信息

• Agaki,S.; Tsuda,K., Chemical and pharmaceutical bulletin, 1961, vol. 9, # 6, p. 464 - 469
  作者：Agaki,S.、Tsuda,K.

  DOI：——

  日期：——
• Agaki,S., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 470 - 475
  作者：Agaki,S.

  DOI：——

  日期：——
• Stary, Ivo; Kocovsky, Pavel, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 5, p. 1227 - 1238
  作者：Stary, Ivo、Kocovsky, Pavel

  DOI：——

  日期：——
• Synthesis of steroidal and nonsteroidal vicinal heterocyclic alcohols, N-(1-cycloalkenyl)heterocycles and their antibacterial studies
  作者：Pallabi Saikia、Partha Pratim Kaishap、Jonalee Goswami、Anil Kumar Singh、Hari Prasanna Deka Boruah、Sanjib Gogoi、Romesh C. Boruah

  DOI：10.1016/j.steroids.2014.03.011

  日期：2014.6

  A solvent free steroidal and nonsteroidal epoxide ring opening reaction by nitrogen containing heterocycles under microwave irradiation is described. Some of the epoxide ring opening compounds were converted to their corresponding N-(1-cycloalkenyl)heterocycles via an acid catalyzed dehydration reaction. The antimicrobial activities of the epoxide ring opening compounds and N-(1-cycloalkenyl)heterocyclic compounds were tested by agar diffusion assay. Compounds 6, 9-12, 24 and 27 showed moderate inhibition against the growth of pathogenic bacteria Escherichia coli, Pseudomonas syringae, Bacillus subtilis, Proteus vulgaris and Staphylococcus aureus. (C) 2014 Elsevier Inc. All rights reserved.