3α,12α-bis(acetoxy)-5Hβ-pregnan-20-one | 15991-93-2

• 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: 3α,12α-bis(acetoxy)-5Hβ-pregnan-20-one
• 英文别名: 3α,12α-diacetoxy-5β-pregnan-20-one；3α,12α-Diacetoxy-5β-pregnanon-(20)；3alpha,12alpha-Dihydroxy-5beta-pregnan-20-one diacetate；[(3R,5R,8R,9S,10S,12S,13S,14S,17S)-17-acetyl-12-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 15991-93-2
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: VYZPGMGWYUEREY-LCLDLZHKSA-N

物化性质

• 沸点：
  490.5±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  3α,12α-bis(acetoxy)-5Hβ-pregnan-20-one 在 Jones reagent 、 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.25h， 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
• 作为产物：
  描述：

  3α,12α-二乙酰氧基-5β-胆烷-24-酸甲酯 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 3α,12α-bis(acetoxy)-5Hβ-pregnan-20-one
  参考文献：
  名称：

  比利时国家经济和发展史托夫分校。65. Mitteilung。噻吩胆甾醇-（3α，12β）-对-（17）

  摘要：

  DOI：

  10.1002/hlca.19430260703

文献信息

• Practical and Modular Construction of C(sp³)-Rich Alkyl Boron Compounds
  作者：Yangyang Yang、Jet Tsien、Ayala Ben David、Jonathan M. E. Hughes、Rohan R. Merchant、Tian Qin

  DOI：10.1021/jacs.0c11964

  日期：2021.1.13

  Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method

  烷基硼酸和酯在富含 C(sp3) 的药物、农用化学品和材料化学的合成中起着重要作用。这项工作描述了一种新型的无过渡金属介导的转化，能够以实用和模块化的方式构建富含 C(sp3) 和空间位阻的烷基硼试剂。通过各种底物，包括与药物化学相关的支架的合成和后期功能化，对该方法的广泛通用性和官能团耐受性进行了广泛检查。这种以烷基硼酸为关键的方法的战略意义通过烷基硼化合物的各种下游功能化得到证明。这种两步并行交叉偶联方法，类似于正式和灵活的烷基-烷基偶联，
• STEROIDS AND RELATED PRODUCTS: XVI. AN IMPROVED SYNTHESIS OF 11-DEHYDRO-17α-METHYLPROGESTERONE
  作者：Ch. R. Engel、G. Just、R. Buttery

  DOI：10.1139/v61-238

  日期：1961.9.1

  An improved synthesis of 11-dehydro-17α-methylprogesterone, previously synthesized by this group, has been devised. The new hormone analogue has the same luteoid activity as 17α-methylprogesterone; in this case, the 11,12-unsaturation has no potentiating effect on the progestational activity. Some stereochemical aspects of the Faworsky rearrangement of 17α-halo-20-keto steroids are discussed in a preliminary fashion.

  一种改进的11-去氢-17α-甲基孕酮的合成方法已被设计出来，此前由该研究小组合成。新的激素类似物具有与17α-甲基孕酮相同的黄体活性；在这种情况下，11,12-不饱和对孕酮活性没有增强作用。对17α-卤代-20-酮类固醇的Faworsky重排的一些立体化学方面进行了初步讨论。
• 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
• Synthesis and Biological Activity of Bile Acid-Derived HMG-CoA Reductase Inhibitors. The Role of 21-Methyl in Recognition of HMG-CoA Reductase and the Ileal Bile Acid Transport System
  作者：Guenther Wess、Werner Kramer、Xiao Bing Han、Klaus Bock、Alfons Enhsen、Heiner Glombik、Karl-Heinz Baringhaus、Georg Boeger、Matthias Urmann

  DOI：10.1021/jm00046a007

  日期：1994.9

  reductase inhibitors by using the specific bile acid transport systems, deoxycholic acid-derived inhibitors 9 and 11 have been synthesized, on the basis of the concept of combining in one molecule structural requirements for specific inhibition of the HMG-CoA reductase and specific recognition by the ileal bile acid transport system. The 1-methyl-3-carboxylpropyl subunit of deoxycholic acid was replaced

  为了通过使用特定的胆汁酸转运系统来提高HMG-CoA还原酶抑制剂的肝选择性，基于将特异性抑制HMG-C的分子结构结合为一个分子的概念，合成了脱氧胆酸衍生的抑制剂9和11。 CoA还原酶和回肠胆汁酸转运系统的特异性识别。脱氧胆酸的1-甲基-3-羧丙基亚基被洛伐他汀的3,5-二羟基庚酸内酯取代，位置12-OH被2-甲基丁酸酯化。评价化合物9和11对大鼠肝脏HMG-CoA还原酶的抑制活性，HEP G2细胞中的胆固醇生物合成以及兔刷状缘膜囊泡中[3 H]牛磺胆酸盐的摄取，并与甲基衍生物8和10进行比较。
• STEROIDS III. 12-METHYLENEPROGESTERONE
  作者：George Just、R. Nagarajan

  DOI：10.1139/v62-057

  日期：1962.2.1

  not available

  无法获取。