3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene | 219562-45-5

• 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: 3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene
• CAS: 219562-45-5
• 化学式: C₂₅H₂₉N₃O₃S
• 分子量: 451.59
• InChiKey: COGMUWDCJJNFMV-RXFVIIJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.13
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以17%的产率得到17α-amino-1,3,5(10)-estratrien-3-ol
  参考文献：
  名称：

  A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis

  摘要：

  The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00063-4
• 作为产物：
  描述：

  3,17β-bis(toluene-4-sulfonyloxy)-1,3,5(10)-estratriene 在 sodium azide 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 120.0h， 以70%的产率得到3-(toluene-4-sulfonyloxy)-17α-azido-1,3,5(10)-estratriene
  参考文献：
  名称：

  A comparative structural study of the steroid epimers: 17β-amino-1,3,5(10)- estratrien-3-ol, 17α-amino-1,3,5(10)-estratrien-3-ol, and some derivatives by 1H NMR, and x-ray diffraction analysis

  摘要：

  The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino-1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-estratrien-3-ol was prepared by catalytic hydrogenation of the estrone-oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosylate, followed by nucleophilic displacement by sodium azide and subsequent reduction with LiAlH4. They were characterized by spectroscopic methods. Determination of the crystal structures of 3-(toluene-4-sulfonyloxy)-17 alpha-azido-1,3,5(10)-estratriene, 3-(toluene-4-sulfonyloxy)-17-alpha-amino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10)-estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratriene enabled us to characterize the structure of the 17 alpha and 17 beta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00063-4