19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione | 194094-44-5

• 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: 19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione
• 英文别名: (8R,9S,10S,13S,14S)-10-[[tert-butyl(dimethyl)silyl]oxymethyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 194094-44-5
• 化学式: C₂₅H₃₈O₃Si
• 分子量: 414.66
• InChiKey: SWMNVZLCDXILSJ-MNUZBTPPSA-N

物化性质

• 沸点：
  496.2±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 雌酚酮
  参考文献：
  名称：

  Templeton, John F.; Lin, Weiyang; Ling, Yangzhi, Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2037 - 2043

  摘要：

  DOI：
• 作为产物：
  描述：

  19-(tert-butyldimethylsiloxy)androst-4-ene-3,17-dione 在 (PhSeO)2O 、 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 20.0h， 以26%的产率得到19-tert-butyldimethylsilyloxy-androsta-1,4-diene-3,17-dione
  参考文献：
  名称：

  Templeton, John F.; Lin, Weiyang; Ling, Yangzhi, Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2037 - 2043

  摘要：

  DOI：

文献信息

• Chemical aromatization of 19-hydroxyandrosta-1,4-diene-3,17-dione with acid or alkaline: Elimination of the 19-hydroxymethyl group as formaldehyde
  作者：Mitsuteru Numazawa、Kouwa Yamashita、Nao Kimura、Madoka Takahashi

  DOI：10.1016/j.steroids.2008.10.011

  日期：2009.2

  In order to determine whether or not a 19-hydroxymethyl group of 19-hydroxyandrosta-1,4-diene-3,17-dione (2,19-hydroxy ADD), an intermediate of aromatase-catalyzed estrone formation from ADD,a suicide substrate of aromatase, is eliminated as formaldehyde, we examine chemical nature of removal of the 19-hydroxymethyl group. 19-Acetate 3 and 19-tert-butyldimethylsiloxy compound 4 are known to convert rapidly to estrone with treatment of NaOH or n-Bu4NF. Since compound 2 was unstable and unobtainable under these conditions, compounds 3 and 4 as equivalents to compound 2 were used in this study. The acetate 3 with 5 mol/l HCl in acetone and 10% KOH in MeOH along with the silyl ether 4 with 5 mol/l HCl in acetone and 1 mol/l n-Bu4NF in THF gave formaldehyde and estrone in which a ratio of the aldehyde to estrone was near 1. This result indicates that the 19-hydroxymethyl groups of compound 3 and 4 are eliminated as formaldehyde along with estrone derived from the steroid skeleton under the acid or base treatment. The findings suggest that a single hydroxylation at the 19 carbon of ADD (1) would be, chemically, all that was required for estrone formation. (C) 2008 Elsevier Inc. All rights reserved.
• Templeton, John F.; Lin, Weiyang; Ling, Yangzhi, Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2037 - 2043
  作者：Templeton, John F.、Lin, Weiyang、Ling, Yangzhi、Majgier-Baranowska, Helena、Marat, Kirk

  DOI：——

  日期：——