18α-acetoxyacetyl-17,18-cyclo-4-androsten-3-one | 81594-18-5

• 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: 18α-acetoxyacetyl-17,18-cyclo-4-androsten-3-one
• CAS: 81594-18-5
• 化学式: C₂₃H₃₀O₄
• 分子量: 370.489
• InChiKey: HBQJLSKGYRMMGC-FCFLTHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  18α-acetoxyacetyl-17,18-cyclo-4-androsten-3-one 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 1.0h， 以0.12 g的产率得到18α-hydroxyacetyl-17,18-cyclo-4-androsten-3-one
  参考文献：
  名称：

  A ring contraction of 18,20-cyclo-steroids. Preparation of 18-acetyl-17,18-cyclo-4-androsten-3-one and 18-hydroxyacetyl-17,18-cyclo-4-androsten-3-one.

  摘要：

  The ring contraction of 18 alpha-mesyloxy-20 alpha-hydroxy-18,20-cyclopregn-4-en-3-one (Ib) and 18 alpha-mesyloxy-20 alpha-hydroxy-21-acetyloxy-18,20-cyclo-pregn-4-en-3-one (Id) took place upon exposure to Florisil at 25 degrees C, producing 18 alpha-acetyl-17,18-cycloandrost-4-en-3-one (IIa) and 18 alpha-acetoxyacetyl-17,18-cycloandrost-4-en-3-one (IIb) respectively. A similar ring contraction of 18 alpha, 20 alpha-dihydroxy-18,20-cyclopregn-4-en-3-one (Ia) took place upon electron impact. Deuterium labeling demonstrated that the first steps of mass spectral fragmentation of Ia were the rearrangement to IIa and the oxidative cleavage to 3,18,20-trioxo-4-pregnene (IVa).

  DOI：

  10.1016/0039-128x(81)90088-x
• 作为产物：
  描述：

  3-oxo-18α,20α-dihydroxy-21-acetoxy-18,20-cyclopregn-4-ene 在 甲基磺酰氯 作用下， 以 吡啶 为溶剂， 反应 20.0h， 以0.34 g的产率得到18α-acetoxyacetyl-17,18-cyclo-4-androsten-3-one
  参考文献：
  名称：

  A ring contraction of 18,20-cyclo-steroids. Preparation of 18-acetyl-17,18-cyclo-4-androsten-3-one and 18-hydroxyacetyl-17,18-cyclo-4-androsten-3-one.

  摘要：

  The ring contraction of 18 alpha-mesyloxy-20 alpha-hydroxy-18,20-cyclopregn-4-en-3-one (Ib) and 18 alpha-mesyloxy-20 alpha-hydroxy-21-acetyloxy-18,20-cyclo-pregn-4-en-3-one (Id) took place upon exposure to Florisil at 25 degrees C, producing 18 alpha-acetyl-17,18-cycloandrost-4-en-3-one (IIa) and 18 alpha-acetoxyacetyl-17,18-cycloandrost-4-en-3-one (IIb) respectively. A similar ring contraction of 18 alpha, 20 alpha-dihydroxy-18,20-cyclopregn-4-en-3-one (Ia) took place upon electron impact. Deuterium labeling demonstrated that the first steps of mass spectral fragmentation of Ia were the rearrangement to IIa and the oxidative cleavage to 3,18,20-trioxo-4-pregnene (IVa).

  DOI：

  10.1016/0039-128x(81)90088-x