3β-acetoxy-19-hydroxycholestan-5-en-24-one | 439797-23-6

• 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: 3β-acetoxy-19-hydroxycholestan-5-en-24-one
• 英文别名: [(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methyl-5-oxoheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 439797-23-6
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: SXPVOIGVOZEPAY-RZJPGGONSA-N

物化性质

• 熔点：
  132-133 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  556.9±30.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-19-hydroxycholestan-5-en-24-one 在 甲酸 、 双氧水 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 16.42h， 生成 24-methylcholest-24(28)-ene-3β,5α,6β,19-tetraol
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (IV): synthesis of 24-methylene-cholesta-3β,5α,6β,19-tetrol, a cytotoxic natural hydroxylated sterol

  摘要：

  The cytotoxic, polyhydroxylated sterol 24-methylene-cholesta-3beta,5alpha,6beta,19-tetrol (1), previously isolated from the soft corals Nephthea albida and N. tiexieral verseveldt, was synthesized using stigmasterol as the starting material by 10 steps in 9% overall yield. The spectral data and physical constants of 1 were identical with those of the natural product. This is the first report of the synthesis of 1. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.002
• 作为产物：
  描述：

  3β-acetoxy-5α-bromo-6β,19-epoxycholestan-24-one 在 锌 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以91%的产率得到3β-acetoxy-19-hydroxycholestan-5-en-24-one
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (IV): synthesis of 24-methylene-cholesta-3β,5α,6β,19-tetrol, a cytotoxic natural hydroxylated sterol

  摘要：

  The cytotoxic, polyhydroxylated sterol 24-methylene-cholesta-3beta,5alpha,6beta,19-tetrol (1), previously isolated from the soft corals Nephthea albida and N. tiexieral verseveldt, was synthesized using stigmasterol as the starting material by 10 steps in 9% overall yield. The spectral data and physical constants of 1 were identical with those of the natural product. This is the first report of the synthesis of 1. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.002