17-acetoxy-3β-benzoyloxyandrosta-5,14,16-triene | 1346236-19-8

• 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: 17-acetoxy-3β-benzoyloxyandrosta-5,14,16-triene
• CAS: 1346236-19-8
• 化学式: C₂₈H₃₂O₄
• 分子量: 432.56
• InChiKey: IFGAPVJHNNDUAG-YDUOIKEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  17-acetoxy-3β-benzoyloxyandrosta-5,14,16-triene 在 palladium 10% on activated carbon 、 甲酸铵 、 碳酸氢钠 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 18.0h， 生成 3β-benzoyloxy-14β-cyanomethylandrost-5-en-17-one
  参考文献：
  名称：

  Diels–Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: Product distribution and selected adduct transformations

  摘要：

  The Diels-Alder cycloaddition of nitroethylene to some androsta-14,16-dien-17-yl acetates has been studied. The addition occurs stereoselectively, giving predominantly head-to-head-adduct. 14 beta-Cyanomethyl steroids were obtained via the reductive cleavage reaction of bridged nitro compounds. The structures of the new compounds have been fully characterized by 2D NMR and tandem mass-spectrometry methods. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.11.015
• 作为产物：
  描述：

  乙酸酐 、 苯甲酰氯 、 17,17-ethylenedioxy-3β-hydroxyandrosta-5,15-diene 在 对甲苯磺酸 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 水 、 丙酮 、 乙酸异丙烯酯 为溶剂， 反应 74.0h， 以1.75 g的产率得到17-acetoxy-3β-benzoyloxyandrosta-5,14,16-triene
  参考文献：
  名称：

  Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data

  摘要：

  On the basis of dehydroepiandrosterone through the Delta(14)- and Delta(15)-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the H-1 and C-13 NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied. DOI: 10.1134/S1070363211090234

  DOI：

  10.1134/s1070363211090234