17β-acetoxy-3β-hydroxyandrost-4-ene

• 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: 17β-acetoxy-3β-hydroxyandrost-4-ene
• 英文别名: [(3S,8R,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: UPBHDNBADOAHCA-BPSSIEEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-acetoxy-3β-hydroxyandrost-4-ene 在 sodium hydroxide 、 双氧水 、 diborane(6) 作用下， 生成 5α-androstane-3β,4α,17β-triol
  参考文献：
  名称：

  Hanson, James R.; Hitchcock, Peter B.; Liman, Mansur D., Journal of the Chemical Society. Perkin transactions I, 1995, # 17, p. 2183 - 2188

  摘要：

  DOI：
• 作为产物：
  描述：

  睾酮 在 吡啶 、 lithium tri-(tert-butoxy)aluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.92h， 生成 17β-acetoxy-3β-hydroxyandrost-4-ene
  参考文献：
  名称：

  对类固醇A环烯烃合成的见解

  摘要：

  经典合成，随后是甾体的纯化甲形环Δ 1烯烃，5 α -雄甾-1-烯-17-酮（5）中，从Δ 1 -3酮烯酮，（5 α，17 β）-3-氧代-5-雄甾-1-烯-17-基乙酸酯（1），通过涉及Δ的反应的策略1 -3-羟基烯丙基醇，3- β羟基-5- α -雄甾-1-烯-17- β基乙酸酯（2）中，用的SOCl 2，是为了重新制备和生物学评价5作为乳腺癌的芳香化酶抑制剂。令人惊讶地，随后策略也得到同分异构的Δ 2烯烃6作为副产物，这只能NMR分析的基础上被检测到。纯化和检测程序的优化使我们可以达到化合物5生物学检测所需的96％纯度。相同的合成策略应用于，使用Δ 4 -3-酮烯酮，3-氧代雄甾-4-烯-17- β -基乙酸甲酯（8），作为起始原料，以制备有效的芳香酶抑制剂Δ 4烯烃，雄甾‐4‐en‐17‐一（15）。出乎意料的是，另一种芳香化酶抑制剂Δ3,5形成了二烯，rost-3,5-dien-

  DOI：

  10.1002/hlca.201300082

文献信息

• Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols
  作者：Pei-Fang Li、Cheng-Bo Yi、Jin Qu

  DOI：10.1039/c5ob00305a

  日期：——

  H2O–1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which are difficult to synthesize by other

  在回流9：1（v / v）H 2 O–1,4-二恶烷且没有其他催化剂的情况下，尝试对各种类型的环丙基甲醇进行重排。发现该反应通常以高至非常高的化学产率得到均烯丙基醇。双环或三环环丙基甲醇的重排容易得到所需的扩环环状均烯丙基醇，其难以通过其他方式合成。
• TESTOSTERONE DERIVATIVES WITH A CARBOXYALKYL SUBSTITUTION IN POSITION 3 AND USE THEREOF FOR THE PRODUCTION OF LABELLED STEROIDS FOR DETERMINING THE CONCENTRATION OF TESTOSTERONE IN A BIOLOGICAL SAMPLE
  申请人：BIOMERIEUX

  公开号：US20150299244A1

  公开（公告）日：2015-10-22

  A testosterone derivative of formula (I): where n is an integer in a range of from 1 to 10, and Y represents an activated or ready-to-be-activated group allowing formation of an amide bond with a primary amine of a molecule. Conjugates including the testosterone derivatives and a marker, methods for determining the concentration of testosterone in a biological sample, and methods for preparing the testosterone derivatives are also provided.

  一种公式为(I)的睾酮衍生物：其中n是1到10范围内的整数，Y代表一个活化或准备激活的基团，允许与分子的初级胺形成酰胺键。还提供了包括睾酮衍生物和标记物的共轭物，用于测定生物样本中睾酮浓度的方法，以及制备睾酮衍生物的方法。
• Baldwin, Derek; Hanson, James R.; Uyanik, Cavit, Journal of Chemical Research, Miniprint, 1999, # 3, p. 1101 - 1114
  作者：Baldwin, Derek、Hanson, James R.、Uyanik, Cavit

  DOI：——

  日期：——
• New Structure–Activity Relationships of A- and D-Ring Modified Steroidal Aromatase Inhibitors: Design, Synthesis, and Biochemical Evaluation
  作者：Carla Varela、Elisiário J. Tavares da Silva、Cristina Amaral、Georgina Correia da Silva、Teresa Baptista、Stefano Alcaro、Giosuè Costa、Rui A. Carvalho、Natércia A. A. Teixeira、Fernanda M. F. Roleira

  DOI：10.1021/jm300262w

  日期：2012.4.26

  A- and D-ring androstenedione derivatives were synthesized and tested for their abilities to inhibit aromatase. In one series, C-3 hydroxyl derivatives were studied leading to a very active compound, when the C-3 hydroxyl group assumes 3 beta stereochemistry (1, IC50 = 0.18 mu M). In a second series, the influence of double bonds or epoxide functions in different positions along the A-ring was studied. Among epoxides, the 3,4-epoxide 15 showed the best activity (IC50 = 0.145 mu M) revealing the possibility of the 3,4-oxiran oxygen resembling the C-3 carbonyl group of androstenedione. Among olefins, the 4,5-olefin 12 (IC50 = 0.135 mu M) revealed the best activity, pointing out the importance of planarity in the A,B-ring junction near C-5. C-4 acetoxy and acetylsalicyloxy derivatives were also studied showing that bulky substituents in C-4 diminish the activity. In addition, IFD simulations helped to explain the recognition of the C-3 hydroxyl derivatives (1 and 2) as well as 15 within the enzyme.
• Diastereoselective hydroformylation of Δ4-steroids with rhodium–phosphite catalysts
  作者：Zoraida Freixa、Mariette M Pereira、J.Carles Bayón、Artur M.S Silva、Jorge A.R Salvador、Ana Matos Beja、José A Paixão、Manuela Ramos

  DOI：10.1016/s0957-4166(01)00191-4

  日期：2001.5

  The hydroformylation of two steroidal substrates, namely 17 beta -acetoxyandrost-4-ene 1 and 3 beta, 17 beta -diacetoxyandrost-4-ene 2, with a rhodium tris(O-tert-butylphenyl)phosphite catalyst was investigated. In both cases, the major reaction product was 4 beta -formyl-17 beta -acetoxy-5 beta -androstane 3, which was isolated and characterized by X-ray diffraction and NMR techniques. This reaction is the first example of catalytic carbonylation to the beta face of a steroid backbone. The effect of reaction temperature, the pressure at which the reaction was completed and the ligand:Rh ratio on the regio- and stereoselectivity of the reaction is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.