4β-bromo-12α-acetoxy-5Hβ-pregnan-3,20-dione | 114276-27-6

• 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: 4β-bromo-12α-acetoxy-5Hβ-pregnan-3,20-dione
• 英文别名: 12α-acetoxy-4β-bromo-5β-pregnane-3,20-dione；12α-Acetoxy-4β-brom-5β-pregnan-3,20-dion
• CAS: 114276-27-6
• 化学式: C₂₃H₃₃BrO₄
• 分子量: 453.417
• InChiKey: DGKKCSSLRSGUHD-GBJCMDETSA-N

物化性质

• 熔点：
  167.4-169.9 °C
• 沸点：
  509.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4β-bromo-12α-acetoxy-5Hβ-pregnan-3,20-dione 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 3β-hydroxy-12α-acetoxy, cyclic 20-(ethylene acetal)pregn-5-ene
  参考文献：
  名称：

  Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii

  摘要：

  14 beta-hydroxy pregnane glycosides extracted from Hoodia gordonii, a succulent plant isolated from Apocynaceae are suggested to have appetite suppressant properties in animals and humans. However, limited reports on biological studies concerning the appetite suppressant properties are available in the open literature. One reason for that is the poor availability of these glycosteroids because H. gordonii is a protected plant and the yield of extraction lies between 0.003% and 0.02%. Starting from 3 alpha,12 alpha-diacetoxy-pregnanone 1, we disclose in this report the synthesis of Hoodigogenin A. the aglycone of the natural 14 beta-hydroxy pregnane glycosides extracted from H. Gordonii. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.014
• 作为产物：
  描述：

  12α-acetoxy-5Hβ-pregnan-3,20-dione 在 溴 、 溶剂黄146 作用下， 反应 1.25h， 生成 4β-bromo-12α-acetoxy-5Hβ-pregnan-3,20-dione
  参考文献：
  名称：

  Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii

  摘要：

  14 beta-hydroxy pregnane glycosides extracted from Hoodia gordonii, a succulent plant isolated from Apocynaceae are suggested to have appetite suppressant properties in animals and humans. However, limited reports on biological studies concerning the appetite suppressant properties are available in the open literature. One reason for that is the poor availability of these glycosteroids because H. gordonii is a protected plant and the yield of extraction lies between 0.003% and 0.02%. Starting from 3 alpha,12 alpha-diacetoxy-pregnanone 1, we disclose in this report the synthesis of Hoodigogenin A. the aglycone of the natural 14 beta-hydroxy pregnane glycosides extracted from H. Gordonii. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.014

文献信息

• TWO-FOLD CYCLOALKYLATIONS OF A BICYCLO[3.3.0]OCTANE-3,7-DIONE
  作者：Eckehard Volker Dehmlow、Hans-Jorg Breyholz、Beate Neumann、Hans-Georg Stammler

  DOI：10.1080/00304940109356607

  日期：2001.8

  5-dicarboxylate with 2-halomethylallyl halides to give cycloheptane derivatives was reported quite recently by Rodriguez et a l . (Eq. Our interest in double ring enlargements of substituted bicyclo[3.3.0]octanes to bicyclo[5.5.0]dodecanes as possible intermediates for certain polycycles,3.4 prompted us to apply this new reaction to compound l.s

  Rodriguez 等人最近报道了一种优雅的三步一锅环扩大环戊酮-2,5-二羧酸二甲酯与 2-卤代甲基烯丙基卤化物的环庚烷衍生物。（方程式：我们对取代双环 [3.3.0] 辛烷双环扩大为双环 [5.5.0] 十二烷作为某些多环的可能中间体的兴趣，3.4 促使我们将这种新反应应用于化合物 ls
• Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 60. Mitteilung. 11-Dehydro-progesteron
  作者：P. Hegner、T. Reichstein

  DOI：10.1002/hlca.19430260303

  日期：1943.5.3
• Steroids and Related Products. IX.¹ The Introduction of the ▵¹¹-Double Bond. I²
  作者：G. JUST、Ch. R. ENGEL

  DOI：10.1021/jo01095a004

  日期：1958.1
• Cyclopentane-polyhydrophenanthrene derivatives
  申请人：WINTHROP CHEM CO INC

  公开号：US02142170A1

  公开（公告）日：1939-01-03