3β-Acetoxycholestan-2-one | 6038-72-8

• 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: 3β-Acetoxycholestan-2-one
• 英文别名: 3β-acetoxy-5α-cholestan-2-one；3β-Acetoxy-5α-cholestan-2-on；2-Oxo-5α-cholestan-3β-yl-acetat；[(3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2-oxo-1,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 6038-72-8
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: DKOFZQMYSDOQHR-FNUGKIMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-Acetoxycholestan-2-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 360.0h， 生成 Di(cholestano<2,3-b:2',3'-e>)pyrazine bis-N-oxide
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052
• 作为产物：
  描述：

  Acetic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-2-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 臭氧 作用下， 生成 3β-Acetoxycholestan-2-one
  参考文献：
  名称：

  类固醇组中的研究。第LXXX部分。制备2-和16-oxo-，3,16-和2,16-dioxo-5α-雄甾烷以及2-oxo-5α-胆甾烷

  摘要：

  从17个酮中分三个阶段即可轻松获得16-Oxo-5α-雄甾烷。，与苯甲醛缩合为16-亚苄基17-酮，氢化铝锂-氯化铝还原为16-亚苄基-雄烷二酮，并进行臭氧分解。此序列不适用于环A中3 → 2的氧代基团的转座。此处，将2-亚芳基-6-酮用硼氢化钠还原并在臭氧分解之前被乙酰化：通过用锌和乙酸还原除去3β-乙酰氧基-2-酮的乙酰氧基。

  DOI：

  10.1039/j39700000244

文献信息

• SYNTHESIS AND CHARACTERIZATION OF PIPERAZINE-2,6-DIONES
  作者：Teresa Mancilla、Lourdes Canillo、Luis S. Zamudio-Rivera、Hiram I. Beltrán、Norberto Farán

  DOI：10.1080/00304940209355746

  日期：2002.2

  Our current interest in piperazine-2,6-dione 3 derivatives of a-amino acids prompted us to develop a methodology to obtain them from a-amino acid methyl ester hydrochlorides 2 and 2bromoacetamide. This paper describes a short, high yield synthesis and characterization of six new piperazine-2,6-diones 3b-g, as well as the known piperazine-2,6-dione 3a via 3+3 annulation. This method provides access to

  哌嗪二酮也称为二酮哌嗪，是最小的环肽，也是几种具有治疗特性的天然产品中的常见基序。研究表明，双二酮哌嗪对 Lewis 肺癌、肉瘤 180、L12 10 白血病、P388 白血病、B 16 骨髓瘤、恶性淋巴瘤、C-26 结肠癌、C-38 人结肠癌和乳腺癌具有抗肿瘤活性。 2-8也被用于临床试验联合治疗？进一步的研究旨在确定这些药物影响细胞生长的机制。'O'~哌嗪-2,6-二酮在第 3 位和第 4 位取代已显示出降血脂活性，3-取代的类似物更具活性，并阐明对小鼠正常和诱导的高脂血症均有效。14 制备哌嗪-2,6-二酮的可用方法很少。它们是由多肽、1sl6 亚氨基二乙酸和甲酸铵，17 通过还原 2,6dibenzyloxypyrazineI8 和用盐酸水解 4-benzyl-2,6-bishydroxyiminopiperazine 制备的。Iy 我们目前对哌嗪-2,6-dione 3 的兴趣α
• The Formation of Five- and Six-membered Rings by the Acyloin Condensation. VI. Cyclization of the Cholesterol a Ring via a 2,3-Secodiester
  作者：John C. Sheehan、William F. Erman

  DOI：10.1021/ja01579a056

  日期：1957.11