13-α-estrone 3-methyl ether oxime | 1704-52-5

• 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: 13-α-estrone 3-methyl ether oxime
• 英文别名: 17-Oximino-13α-Δ^1,3,5(10)-oestratrien-3-ol-3-methylether
• CAS: 1704-52-5
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: UPFPBOLHKZHRQR-VXIBKDFQSA-N

物化性质

• 熔点：
  138-141 °C
• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  13-α-estrone 3-methyl ether oxime 在 吡啶 、 对甲苯磺酰氯 作用下， 以53%的产率得到3-methoxy-17a-aza-13-α-D-homoestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Synthesis of N-[2-(2-pyridyl)ethyl]-17a-aza-d-homosteroids and their biomimetic copper-mediated ligand hydroxylations with molecular oxygen

  摘要：

  Starting with the oximes of 3-O-methylestrone and 3-O-methyl-13alpha-estrone we have synthesized 17a-aza steroids as chiral trans- and cis-fused piperidines via a Beckmann rearrangement. These could then be transformed to the corresponding N-[2-(2-pyridyl)ethyl]-17a-aza-steroids. Copper(I) complexes of these bidentate ligands bind and activate molecular oxygen. While the cis-azasteroids are inert towards hydroxylation, in the trans-series hydroxylation occurs beta to the N-atom on the ring (C-16) and in the side chain: The former hydroxylation is completely stereoselective with only the (16R)-epimer being produced while the latter oxidation occurs with low stereoselectivity. The influence of how the copper(I) complexes were prepared on the oxidation behavior is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00362-8
• 作为产物：
  描述：

  3-methoxy-13α-estra-1,3,5(10)-trien-17-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以91%的产率得到13-α-estrone 3-methyl ether oxime
  参考文献：
  名称：

  Synthesis of N-[2-(2-pyridyl)ethyl]-17a-aza-d-homosteroids and their biomimetic copper-mediated ligand hydroxylations with molecular oxygen

  摘要：

  Starting with the oximes of 3-O-methylestrone and 3-O-methyl-13alpha-estrone we have synthesized 17a-aza steroids as chiral trans- and cis-fused piperidines via a Beckmann rearrangement. These could then be transformed to the corresponding N-[2-(2-pyridyl)ethyl]-17a-aza-steroids. Copper(I) complexes of these bidentate ligands bind and activate molecular oxygen. While the cis-azasteroids are inert towards hydroxylation, in the trans-series hydroxylation occurs beta to the N-atom on the ring (C-16) and in the side chain: The former hydroxylation is completely stereoselective with only the (16R)-epimer being produced while the latter oxidation occurs with low stereoselectivity. The influence of how the copper(I) complexes were prepared on the oxidation behavior is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00362-8