2α,3α-epoxycholestan-5α-ol | 14335-49-0

• 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: 2α,3α-epoxycholestan-5α-ol
• 英文别名: 5α-Hydroxycholestan-2α,3α-epoxid；2α,3α-epoxy-5α-cholestan-5-ol；(1S,2R,4R,6S,8R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-8-ol
• CAS: 14335-49-0
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: JGCBUDSKGHJASF-FUARUQEFSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  489.2±18.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2α,3α-epoxycholestan-5α-ol 在 吡啶 、 碘 、 magnesium 作用下， 反应 3.5h， 生成 2β-(2'-propenyl)cholestane-3α,5α-diol 3-acetate
  参考文献：
  名称：

  Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction

  摘要：

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.

  DOI：

  10.1021/jo00095a012
• 作为产物：
  描述：

  3β-Tosyloxy-5α-cholestanol-(5) 在 aluminum oxide 、 单过氧邻苯二甲酸 、 乙醇 作用下， 生成 2α,3α-epoxycholestan-5α-ol
  参考文献：
  名称：

  Clayton et al., Journal of the Chemical Society, 1957, p. 1982,1990

  摘要：

  DOI：

文献信息

• Komeno,T. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 1145 - 1160
  作者：Komeno,T. et al.

  DOI：——

  日期：——
• Komeno,T.; Itani,H., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 3, p. 608 - 616
  作者：Komeno,T.、Itani,H.

  DOI：——

  日期：——
• Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto, J. Org. Chem, 59 (1994) N 16, S 4393-4401
  作者：Boto Alicia, Betancor Carmen, Prange Thierry, Suarez Ernesto

  DOI：——

  日期：——
• Clayton et al., Journal of the Chemical Society, 1957, p. 1982,1990
  作者：Clayton et al.

  DOI：——

  日期：——
• Fragmentation of Alkoxy Radicals: Tandem .beta.-Fragmentation-Cycloperoxyiodination Reaction
  作者：Alicia Boto、Carmen Betancor、Thierry Prange、Ernesto Suarez

  DOI：10.1021/jo00095a012

  日期：1994.8

  The steroidal alcohols 2-cholesten-5 alpha-ol (3), 3-phenyl-2-cholesten-5 alpha-ol (4), and 3 alpha H-2'-oxofuro-[2,3]cholestan-5 alpha-ol (5) were prepared in order to test a new tandem beta-fragmentation-cycloperoxyiodination reaction. The alkoxy radicals generated by irradiation of these alcohols with visible light in the presence of (diacetoxyiodo)benzene, I-2, and molecular oxygen undergo a beta-fragmentation reaction with subsequent peroxidation of the C-radical formed. This peroxy radical is added to conveniently positioned double bonds to give 10-membered cyclic ketones possessing a 1,2-dioxolane group.