5β-pregn-3-en-20-one | 62054-02-8

• 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: 5β-pregn-3-en-20-one
• 英文别名: 5β-pregnen-(3)-one-(20)；5β-Pregnen-(3)-on-(20)；5beta-Pregn-3-en-20-one；1-[(5R,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 62054-02-8
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: AMNWULQVHOJWMK-QGVNFLHTSA-N

物化性质

• 熔点：
  136-139 °C
• 沸点：
  392.6±42.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5beta-孕甾烷-3,20-二酮	pregnanedione	128-23-4	C21H32O2	316.484
  黄体酮	Progesterone	57-83-0	C21H30O2	314.468
  孕烯醇酮	Pregnenolone	145-13-1	C21H32O2	316.484

反应信息

• 作为产物：
  描述：

  黄体酮 在 甲酸 、 锌 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 生成 5β-pregn-3-en-20-one
  参考文献：
  名称：

  14 .beta.-Hydroxy 3-deoxycardenolides

  摘要：

  揭示了作为药用化合物有用的公式##STR1##的新化合物。还公开了它们的制备方法。

  公开号：

  US04102884A1

文献信息

• Synthesis of Fluorinated Steroids Using a Novel Fluorinating Reagent Tetrabutylammonium Difluorodimethylphenylsilicate (TAMPS)
  作者：Pavel Herrmann、Jaroslav Kvíčala、Vladimír Pouzar、Hana Chodounská

  DOI：10.1135/cccc20081825

  日期：——

  Steroidal 3-fluoroderivatives were prepared from corresponding tosylates using tetrabutylammonium difluorodimethylphenylsilicate as fluorinating agent. The reaction was tested on all four possible C-3 and C-5 stereoisomers of cholestane and 17-oxoandrostane skeletons. In this reaction only one isomer was always formed with opposite configuration at C-3 to starting tosylate. The reaction is accompanied by elimination which affords a mixture of corresponding olefines.

  使用四丁基铵二氟二甲基苯基硅酸酯作为氟化试剂，从相应的tosylates制备了类固醇3-氟衍生物。该反应在胆甾烷和17-氧基雄甾烷骨架的所有四个可能的C-3和C-5立体异构体上进行了测试。在这个反应中，只形成了一个异构体，其C-3位置的构型与起始的tosylate相反。该反应伴随着消除作用，产生相应的烯烃混合物。
• Butenandt; Westphal, Chemische Berichte, 1934, vol. 67, p. 2085,2087
  作者：Butenandt、Westphal

  DOI：——

  日期：——
• Neurosteroids: Can a 2alpha,3alpha-epoxy ring make up for the 3alpha-hydroxyl group?
  作者：Alexander Kasal、Miloš Buděšínský、Pavel Mareš、Zdena Krištofíková、Alcino J. Leitão、Maria Luisa Sá e Melo、Maria Manuel C. Silva

  DOI：10.1016/j.steroids.2015.11.007

  日期：2016.1

  Seven steroid epoxides were prepared from 5 alpha-pregn-2-en-20-one and 5 alpha-pregn-3-en-20-one and their side-chain derivatives. All compounds were tested in vitro for binding to gamma-aminobutyric acid (GABA(A)) receptor, some of them also in vivo for anticonvulsant action.2 alpha,3 alpha-Epoxy-5 alpha-pregnan-20-one inhibited the TBPS binding to the GABA(A) receptor and showed a moderate anticonvulsant action in immature rats. In contrast, its 3 alpha,4 alpha-isomer was inactive. More polar epoxide derivatives, modified at the side chain were less active or inactive.Noteworthy, diol 20, the product of trans-diaxial opening of the 2 alpha,3 alpha-epoxide 4, was not able to inhibit the TBPS binding, showing that the activity of the epoxide is due to the compound itself and not to its hydrolytic product.The 3 alpha-hydroxyl group is known to be essential for the GABA(A) receptor binding. Despite the shortness of in vivo effects which are probably due to metabolic inactivation of the products prepared, our results show that the 2 alpha,3 alpha-epoxy ring is another structural pattern with ability to bind the GABA(A)R. (C) 2015 Elsevier Inc. All rights reserved.
• Schmitt,J. et al., Bulletin de la Societe Chimique de France, 1962, p. 1846 - 1855
  作者：Schmitt,J. et al.

  DOI：——

  日期：——
• US4102884A
  申请人：——

  公开号：US4102884A

  公开（公告）日：1978-07-25