3-methoxy-16β-(benzylaminomethyl)estra-1,3,5(10)-trien-17-one | 878289-24-8

• 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: 3-methoxy-16β-(benzylaminomethyl)estra-1,3,5(10)-trien-17-one
• 英文别名: (8R,9S,13S,14S,16R)-16-[(benzylamino)methyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 878289-24-8
• 化学式: C₂₇H₃₃NO₂
• 分子量: 403.565
• InChiKey: FNIRDEKIBIWQSB-QEJWLFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-16β-(benzylaminomethyl)estra-1,3,5(10)-trien-17-one 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到3-methoxy-16β-(benzylaminomethyl)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：

  3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one 、 苄胺 在 氢氧化钾 作用下， 以85%的产率得到3-methoxy-16β-(benzylaminomethyl)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Synthesis of some novel D-ring-fused dioxa- and oxazaphosphorinanes in the estrone series

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.12.038

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.
• New steroid-fused P-heterocycles
  作者：Éva Frank、Brigitta Kazi、Zoltán Mucsi、Krisztina Ludányi、György Keglevich

  DOI：10.1016/j.steroids.2007.02.001

  日期：2007.5

  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.