3β-acetoxyandrost-5-ene | 13067-44-2

• 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: 3β-acetoxyandrost-5-ene
• 英文别名: 3β-acetoxy-androst-5-en-3-ol；3β-acetoxy-androst-5-ene；3β-acetoxyl-5-androstene；3β-Acetoxy-androst-5-en；(10R)-3c-Acetoxy-10r.13c-dimethyl-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-(androsten-(5)-yl-(3β)-ester)；3beta-Acetoxyandrost-5-ene；[(3S,8S,9S,10R,13S,14S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 13067-44-2
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: XJBMGBWQXGCCNJ-PXQJOHHUSA-N

物化性质

• 熔点：
  95.5-97 °C
• 沸点：
  399.2±21.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-acetoxyandrost-5-ene 在 potassium permanganate 、 iron(III) perchlorate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 以75%的产率得到5α-hydroxy-6-oxoandrostane-3β-yl acetate
  参考文献：
  名称：

  One-pot, high yield synthesis of α-ketols from Δ5-steroids

  摘要：

  a-Hydroxy ketones (alpha-ketols) are present in many compounds with biological activity. Several methods are available for the preparation of alpha-ketols but only a few of them describe the synthesis of steroid alpha-ketols from olefins. In this work, a new system consisting of KMnO4/Fe(ClO4)(3)center dot nH(2)O was used in order to achieve the direct conversion of Delta(5)-steroids to their corresponding alpha-ketols, in high yields. Consideration of the probable reaction mechanism is provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to assign H-1 and C-13 resonances of some synthesized compounds. This method has potential for the preparation of alpha-hydroxy ketones of biological interest. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.11.002
• 作为产物：
  描述：

  3β-acetoxyetienic acid 在 吡啶 、 草酰氯 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.75h， 生成 3β-acetoxyandrost-5-ene
  参考文献：
  名称：

  类固醇和性激素。第262部分：自由基诱导的硒酸酯和硒代碳酸酯的锡烷还原：一种将羧酸降解为正烷烃以及将醇脱氧为烷烃的新方法†

  摘要：

  通过常规方法，由羧酸形成的碳硒烯酸酯与三丁基锡氢化物在惰性芳族溶剂中反应，取决于反应温度和母体羧酸的结构，通过加热生成相应的醛或相应的烷烃，或通过当主要以高产率形成醛时，在环境温度下进行紫外线照射。在α，β-不饱和碳硒烯酸酯的情况下，热反应仅导致相应的醛。

  DOI：

  10.1002/hlca.19800630823

文献信息

• The reaction of lead tetraacetate with 3.BETA.-hydroxy steroids.
  作者：RIKIO OHUCHI、KENYU SHIBATA、NOBUAKI YAMAKOSHI、HIROMU MORI

  DOI：10.1248/cpb.29.43

  日期：——

  It was found that the reaction of lead tetraacetate with 3β-hydroxy steroids of the 5α-series gave the corresponding 3β, 19-oxido steroids. Only poor yields were obtained in the cases of 3β-hydroxy steroids having no substituent at C-5 (5α-H). Substitution at the 5α-position by an electronegative group such as halogen or acetoxyl enhanced the yield of the 3β, 19-oxido compound. The best result was obtained when a steroid was heated with lead tetraacetate in benzene in the presence of calcium carbonate and a trace of benzoyl peroxide.

  发现四乙酸铅与5α系列3β-羟基甾体化合物的反应产生了相应的3β, 19-氧代甾体化合物。在没有C-5（5α-H）取代基的3β-羟基甾体化合物的情况下，仅得到了较低的产率。通过在5α位引入电负性基团如卤素或乙酰氧基能提高3β, 19-氧代化合物的产率。当甾体化合物在碳酸钙和微量过氧化苯甲酰存在下，与四乙酸铅在苯中加热时，得到了最佳结果。
• Aqueous Reduction of Iodosteroids to Deoxysteroids
  作者：Changsheng Liu、Lili Sun、Chunbao Li

  DOI：10.3184/174751914x13968892307636

  日期：2014.5

  A new method for the reduction of iodosteroids to deoxysteroids has been developed using Zn, HCOOH and a catalytic amount of Aliquat 336 in water. In total, 13 iodosteroids were reduced in good to excellent yields. The higher solubilities of the substrates lead to the faster reactions, and the aqueous reaction was efficiently accelerated by granular polytetrafluoroethylene. The advantage of the aqueous system over eight organic solvents has also been demonstrated.

  利用 Zn、HCOOH 和催化量的 Aliquat 336 在水中还原碘甾类化合物为脱氧甾类化合物的新方法已经开发出来。共还原出 13 种碘甾类化合物，收率从良好到极佳。底物的溶解度越高，反应速度越快，粒状聚四氟乙烯能有效加速水反应。水性体系相对于八种有机溶剂的优势也得到了证实。
• Allylic and benzylic oxidation using cobalt(II) alkyl phosphonate modified silica
  作者：Magdalena Jurado-Gonzalez、Alice C. Sullivan、John R.H. Wilson

  DOI：10.1016/s0040-4039(03)00833-5

  日期：2003.5

  The allylic and benzylic oxidation of a range of substrates proceeds in good yield using catalytic quantities of cobalt(II) alkyl phosphonate modified silica and tert-butyl hydroperoxide.

  使用催化量的烷基膦酸钴（II）改性的二氧化硅和叔丁基氢过氧化物，可以以良好的收率进行一系列底物的烯丙基和苄基氧化反应。
• The allylic oxidation of unsaturated steroids by tert-butyl hydroperoxide using homogeneous and heterogeneous cobalt acetate
  作者：Jorge A. R. Salvador、James H. Clark

  DOI：10.1039/b007447k

  日期：——

  Cobalt acetate is an effective catalyst for the selective allylic oxidation of unsaturated steroids using tert-butyl hydroperoxide especially when used in a supported form when it can be easily recovered and reused.

  乙酸钴是使用叔丁基过氧化氢对不饱和类固醇进行选择性烯丙基氧化的有效催化剂，特别是当它以易于回收和再利用的负载形式使用时。
• The 16,17-Double Bond Is Needed for Irreversible Inhibition of Human Cytochrome P450₁₇_α by Abiraterone (17-(3-Pyridyl)androsta-5,16-dien-3β-ol) and Related Steroidal Inhibitors
  作者：Michael Jarman、S. Elaine Barrie、Jose M. Llera

  DOI：10.1021/jm981017j

  日期：1998.12.1

  drost-5-en-3beta-ol (5) and 17beta-(3-pyridyl)-16,17alpha-epoxy-5alpha-androst-3beta-ol (6) were synthesized. 3beta-Acetoxyetienic acid was converted in three steps into 5 via photolysis of the thiohydroxamic ester 8. Oxidation of an appropriate 16,17-unsaturated precursor (21) with CrO3-pyridine afforded the acetate (23) of 6. Inhibition of the enzyme by 1, the similarly potent 5,6-reduced analogue

  阿比特龙（17-（3-吡啶基）androsta-5,16-dien-3beta-ol，1）是一种有效的抑制剂（对人细胞色素P45017alpha的IC50为4 nM羟化酶）。为了协助研究16,17-双键在其作用机理中的作用，新型17alpha-（4-吡啶基）androst-5-en-3beta-ol（5）和17beta-（3-吡啶基）合成了-16,17alpha-环氧-5alpha-androst-3beta-ol（6）。通过硫代异羟肟酸酯8的光解反应，可将3β-乙酰氧基烯酸分三步转化为5。适当的16,17-不饱和前体（21）用CrO3-吡啶氧化得到乙酸盐（23）。6 1，同样有效的5,6-还原类似物19（IC50 5 nM），4、16 dien-3-one 26（IC50 3 nM）和效价较低的（IC50 13 nM）3,5，16 -三烯25的发生较慢，但通过将抑制剂与酶预孵育而增强。与