4α,5α-epoxycholestan-3β-yl acetate | 1256-52-6

• 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: 4α,5α-epoxycholestan-3β-yl acetate
• 英文别名: acetic acid-(4α,5-epoxy-5α-cholestan-3β-yl ester)；Essigsaeure-(4α,5-epoxy-5α-cholestan-3β-ylester)；3β-Acetoxy-4α,5-epoxy-5α-cholestan；3β-Acetoxy-4α,5α-epoxy-cholestan；4,5α-Epoxy-cholestan-ol-(3β)-acetat；[(1S,2R,5S,6R,8S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadecan-5-yl] acetate
• CAS: 1256-52-6
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: HXKDHGZOPCTTAY-QUSHEWTOSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  506.5±33.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4α,5α-epoxycholestan-3β-yl acetate 在 铂 吡啶 、 氯化亚砜 、 氢气 作用下， 以 乙醚 为溶剂， 生成 3β-Acetoxy-4-methyl-5α-cholestan
  参考文献：
  名称：

  Julia,S.; Lavaux,J.-P., Bulletin de la Societe Chimique de France, 1963, p. 1223 - 1230

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 过氧化氢苯甲酰 、 苯 作用下， 生成 4α,5α-epoxycholestan-3β-yl acetate
  参考文献：
  名称：

  376.立体化学的各个方面。第一部分：由环状烯丙基醇形成环氧化物的立体特异性

  摘要：

  DOI：

  10.1039/jr9570001958

文献信息

• Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate
  作者：João F.S. Carvalho、M. Manuel Cruz Silva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2009.01.100

  日期：2009.4

  Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations

  通过在回流温度下使用悬浮在乙腈（CH 3 CN）中的双（双过氧邻苯二甲酸酯）六水合镁（MMPP）作为氧化剂，可以从相应的均烯丙基和烯丙基甾体烯烃快速生成环氧化物。该方案涉及使用安全易得的氧化剂以及易于后处理的方法，这使该过程非常有效。据报道类固醇的选择性4，5-和5，6-环氧化。其中，Δ的高立体选择性环氧化5 -B去甲胆甾烷达到了。而且，该方法对5，6-位是化学选择性的，可用于环A烯酮的环氧化。
• Reactions of epoxides—II
  作者：J.M. Coxon、M.P. Hartshorn、D.N. Kirk

  DOI：10.1016/s0040-4020(01)90833-6

  日期：1964.1

  3β-Acetoxy-4α,5-epoxy-5α-cholestane is rearranged by boron trifluoride to give 3β-acetoxy-5β-cholestan-4-one (IV). Under similar reaction conditions the 3α-acetox-4β,5β-epoxide gives a stable 3α,5α-bridged ionic complex, and the 3β-acetoxy-4β,5β epoxide gives the fluorohydrin (X).

  用三氟化硼将3β-乙酰氧基-4α，5-环氧-5α-胆甾烷重排，得到3β-乙酰氧基-5β-胆甾烷-4-酮（IV）。在相似的反应条件下，3α-乙酰氧基-4β，5β-环氧化物生成稳定的3α，5α-桥联离子络合物，3β-乙酰氧基-4β，5β环氧化物生成氟代醇（X）。
• Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm9003973

  日期：2009.7.9

  A library of diastereomerically pure epoxysterols, prepared by combining chemical and enzymatic methodologies, was evaluated for cytotoxicity toward human cancer and noncancer cell lines. Unsaturated steroids were oxidized by magnesium bis(monoperoxyphthal ate) hexahydrate in acetonitrile, and the resulting epimeric epoxides were enzymatically separated using Novozym 435 or lipase AY. Some of the synthesized epoxysterols have potent cytotoxicity and higher activity on cancer cell lines HT29 and LAMA-84.
• 376. Aspects of stereochemistry. Part I. Stereospecificity in formation of epoxides from cyclic allylic alcohols
  作者：H. B. Henbest、R. A. L. Wilson

  DOI：10.1039/jr9570001958

  日期：——
• Coexistence of two species of <i>Halipeurus</i> (Phthiraptera) on Chatham Island taiko (<i>Pterodroma magentae</i>) (Aves)
  作者：Ricardo L. Palma、Michael J. Imber

  DOI：10.1080/03014223.2000.9518230

  日期：2000.1

  Feather lice (Phthiraptera) were collected from 14 Chatham Island taiko (Pterodroma magentae). These included two species of Halipeurus (Philopteridae) in the ratio of two H. procellariae to one H. theresae. So far as we know, the regular occurrence of two Halipeurus species on a host is unique. H. procellariae is likely to have been acquired from the taiko's ancestors, but H. theresae probably derives from a secondary infestation through close association of the host with Chatham petrels (Pterodroma axillaris), probably in mixed breeding colonies. From sub-fossil evidence, Chatham petrels formerly bred on the main Chatham Island, to which P. magentae has, from such evidence, always been restricted.