17β-hydroxy-16β-aminomethylestrone 3-methyl ether | 218281-26-6

• 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: 17β-hydroxy-16β-aminomethylestrone 3-methyl ether
• 英文别名: (8R,9S,13S,14S,16R,17S)-16-(aminomethyl)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 218281-26-6
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: MBGQPJAJDKKIJE-FTVOKIHPSA-N

物化性质

• 沸点：
  473.295±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-16β-aminomethylestrone 3-methyl ether 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 3-methoxy-16β-((4'-fluorobenzylamino)methyl)estra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  New steroid-fused P-heterocycles

  摘要：

  16(beta-Aminomethyl-17 beta-hydroxyestrone 3-methyl ether 6 and its N-propyl (17), N-benzyl (18) and N-arylmethyl derivatives (19-22) were subjected to ring closure reactions with phenylphosphonic dichloride in order to synthetize P-epimeric oxazaphosphorinanes 23a, 24-29 in which the hetero ring is condensed to ring D of the sterane skeleton. The stereostructures of the products were evaluated by H-1, C-13 and P-31 NMR spectroscopy. The geometry was optimized by utilizing the B3LYP DFT method. The NMR spectral data and the results of the ab initio calculations demonstrated that the stereostructure of the hetero ring was strongly affected by the rigid sterane framework condensed to it, and the phosphoramidate ring proved to adopt predominantly a distorted-boat conformation, regardless of the P-configuration. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.02.001
• 作为产物：
  描述：

  16β-azidomethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以88%的产率得到17β-hydroxy-16β-aminomethylestrone 3-methyl ether
  参考文献：
  名称：

  One-Step Conversion of Oxetane-Fused to 1,3-Oxazine-Fused Steroids

  摘要：

  在一个环扩张反应中，烷基和芳基腈在四氟硼酸二乙醚络合物存在下，与3-甲氧基-16β,17β-二氢-4'H-氧蒽并[3',2':16,17]雌三烯反应，生成3-甲氧基-16β,17β-二氢-4'H-[1,3]-噁唑啉[5',6':16,17]雌三烯衍生物。在类似条件下，3-甲氧基-16α,17α-二氢-4'H-氧蒽并[3',2':16,17]雌三烯会发生瓦格纳-梅尔文重排反应。

  DOI：

  10.1135/cccc19981613

文献信息

• Synthesis of some novel D-ring-fused dioxa- and oxazaphosphorinanes in the estrone series
  作者：Éva Frank、Brigitta Kazi、Krisztina Ludányi、György Keglevich

  DOI：10.1016/j.tetlet.2005.12.038

  日期：2006.2

  New types of P-heterocyclic-fused steroids, such as dioxa- and oxazaphosphorinane derivatives, were synthetized from estrone-1,3-dihydroxy and 1,3-aminoalcohol precursors by cyclization with phenylphosphonic dichloride. (c) 2005 Elsevier Ltd. All rights reserved.