5α-androst-16-en-3β-yl acetate | 72203-76-0

• 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: 5α-androst-16-en-3β-yl acetate
• 英文别名: 3β-Acetoxy-5α-androst-16-en；3β-Acetoxy-5α-androsten-16；3β-acetoxy-(5α)-androst-16-ene；Essigsaeure-(5α-androst-16-en-3β-ylester)；[(3S,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 72203-76-0
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: MUSSUDIZUKJZHB-BPSSIEEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 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：

  5α-androst-16-en-3β-yl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (3B,5A)-雄甾-16-烯-3-醇
  参考文献：
  名称：

  Francisco, Cosme G.; Freire, Raimundo; Hernandez, Rosendo, Journal of the Chemical Society. Perkin transactions I, 1983, p. 297 - 304

  摘要：

  DOI：
• 作为产物：
  描述：

  17α-Brom-3β-acetoxy-5α-androstanon-(16) 在 sodium hydroxide 、 sodium tetrahydroborate 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 5α-androst-16-en-3β-yl acetate
  参考文献：
  名称：

  Fajkos,J.; Joska,J., Collection of Czechoslovak Chemical Communications, 1961, vol. 26, p. 1118 - 1136

  摘要：

  DOI：

文献信息

• Pd-mediated cross-coupling of C-17 lithiated androst-16-en-3-ol – access to functionalized arylated steroid derivatives
  作者：Vanessa Koch、Stefan Bräse

  DOI：10.1039/c6ob02496c

  日期：——

  we report on Pd-mediated cross-coupling of vinyllithium steroids and aryl bromides to introduce various substituted aryls at C-17 of steroidal frameworks based on the structure of epi-androsterone. Compared to other C–C cross-couplings, this method turned out to be an easy and competitive access to biologically interesting C-17 modified steroids.

  在本文中，我们报道了基于表位-雄甾酮结构的Pd介导的乙烯基锂类固醇和芳基溴化物的交叉偶联，以在类固醇骨架的C-17处引入各种取代的芳基。与其他C–C交叉偶联相比，该方法证明是一种容易获得生物竞争性C-17修饰类固醇的竞争产品。
• Stille and Suzuki Cross-Coupling Reactions as Versatile Tools for Modifications at C-17 of Steroidal Skeletons - A Comprehensive Study
  作者：Vanessa Koch、Martin Nieger、Stefan Bräse

  DOI：10.1002/adsc.201601289

  日期：2017.3.6

  cross‐coupling study of steroidal vinyl (pseudo)halides with different boronic acids and tributyltin organyls. Furthermore, we have investigated the “inverse” case of those cross‐coupling reactions, i.e., the reaction of a steroidal vinylpinacolatoborane or a tributyltin steroid with various bromides. The development of both methods allows the introduction of different residues at C‐17 of steroid skeletons

  本文中，我们报告了甾体乙烯基（假）卤化物与不同的硼酸和三丁基锡有机基的Stille和Suzuki交叉偶联的比较研究。此外，我们研究了那些交叉偶联反应的“逆向”情况，即类固醇乙烯基松香烷硼烷或三丁基锡类固醇与各种溴化物的反应。两种方法的发展都允许在类固醇骨架的C-17处引入不同的残基，从而提供了广泛的类固醇类似物的途径，这对于生物学筛选或天然产物合成非常重要。
• Studies Towards the Total Synthesis of Di- and Sesterterpenes with Dicyclopenta[a,d]cyclooctane Skeletons. Three-component Approach to the A/B Rings Building Block
  作者：K. Michalak、M. Michalak、J. Wicha

  DOI：10.3390/10091084

  日期：——

  fusicoccin families are important synthetic targets because of complexity of structure and potentially useful physiological activities, including anti-tumor activity. A synthesis of versatile building blocks for these terpenoids is described. Cyclopenta[8]annulene rings system with properly dislocated substituents was constructed using as key steps ring closing metathesis reaction and Wagner - Meerwein

  由于结构的复杂性和潜在有用的生理活性（包括抗肿瘤活性），倍半萜烯和二萜类化合物是重要的合成靶标。描述了这些萜类化合物的通用构件的合成。使用作为关键步骤的闭环复分解反应和Wagner-Meerwein重排构建了具有适当错位取代基的环戊二烯[8]环系统。详细研究了导致环戊二烯[8]环烯的闭环复分解反应。
• Synthetische Verwendung von Epoxynitronen. II. Synthese von Steroid-?-methyliden-?-lactonen
  作者：Martin Riediker、Walter Graf

  DOI：10.1002/hlca.19790620524

  日期：1979.7.17

  Synthetic application of epoxynitrones. II. Syntheses of steroidal α-methylidene-γ-lactones

  环氧硝酮的合成应用。二。甾族α-亚甲基-γ-内酯的合成
• Practical synthesis of androgen: the efficient transformation of 17-oxo group to 17α-hydroxy group
  作者：Tetsuo Ohta、Huyue Zhang、Yoshitaka Torihara、Takemasa Hida、Isao Furukawa

  DOI：10.1016/s0039-128x(98)00067-1

  日期：1998.12

  The present report describes the improved transformation of the 17-oxo group in 3 beta-acetoxy-5 alpha-androstan-17-one to a 17 alpha-hydroxy group. A mixture of 17 alpha-acetoxy and 16-ene compounds, which are usually produced by the standard synthetic route, were treated with peracetic acid (epoxidation of the 16-ene compound) and then sodium hydroxide (reduction-hydrolysis) to give the desired 17 alpha-hydroxy compound in much better yield than that in previous reports. Recrystallization of the crude product with cyclohexane-methanol gave the pure compound in 54% yield (total yield from starting ketone). (Steroids 63:630-632). (C) 1998 by Elsevier Science Inc.