5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate | 2723-07-1

• 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: 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate
• 英文别名: 3-Acetat v. 5α-Brom-3β,6β-dihydroxy-pregnan-20-on
• CAS: 2723-07-1
• 化学式: C₂₃H₃₅BrO₄
• 分子量: 455.432
• InChiKey: IHMAWSPONHJXAS-CDBJEIEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 在 calcium carbonate 作用下， 以 吡啶 、 N,N-二甲基乙酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol

  摘要：

  Starting from stigmasterol (2), 24-methylenecholest-4-en-3 beta ,6 beta -diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3 beta -acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3 beta, 6 beta -diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00132-x
• 作为产物：
  描述：

  17(α,β)-Pregnen-3β-ol-20-on-acetat 在 高氯酸 、 N-溴代乙酰胺 作用下， 以 水 为溶剂， 以61%的产率得到5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol

  摘要：

  Starting from stigmasterol (2), 24-methylenecholest-4-en-3 beta ,6 beta -diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3 beta -acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3 beta, 6 beta -diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00132-x