3β-benzoyloxy-14β-cyanomethylandrosta-5,15-dien-17-one | 1422183-15-0

• 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: 3β-benzoyloxy-14β-cyanomethylandrosta-5,15-dien-17-one
• 英文别名: [(3S,8R,9S,10R,13S,14R)-14-(cyanomethyl)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,11,12-octahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 1422183-15-0
• 化学式: C₂₈H₃₁NO₃
• 分子量: 429.559
• InChiKey: GFMHJYGHLBLHDD-ZQDGRCEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-benzoyloxy-14β-cyanomethylandrosta-5,15-dien-17-one 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到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：

  3β-benzoyloxy-14,17-etheno-16α-nitroandrost-5-en-17β-yl acetate 在 碳酸氢钠 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到3β-benzoyloxy-14β-cyanomethylandrosta-5,15-dien-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

文献信息

• Diels–Alder reaction of androsta-14,16-dien-17-yl acetates with nitroethylene: Product distribution and selected adduct transformations
  作者：Alexander V. Baranovsky、Dmitry A. Bolibrukh、Vladimir A. Khripach、Bernd Schneider

  DOI：10.1016/j.steroids.2012.11.015

  日期：2013.2

  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.