5,6β-epoxy-5β-cholestan-3α-ol acetate | 14456-17-8

• 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: 5,6β-epoxy-5β-cholestan-3α-ol acetate
• 英文别名: 5,6β-epoxy-5β-cholestan-3α-yl acetate；3α-acetoxy-5β,6β-epoxycholestane；5β,6β-epoxy-3α-acetoxycholestane；3α-Acetoxy-5,6β-epoxy-5β-cholestan；5beta,6beta-Epoxy-3alpha-acetoxycholestane；[(1S,2R,5R,7S,9R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl] acetate
• CAS: 14456-17-8
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: VEEBKUQFPONGGR-OAQJTHNDSA-N

物化性质

• 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：

  5,6β-epoxy-5β-cholestan-3α-ol acetate 以 氯仿 为溶剂， 反应 48.0h， 以0.06 g的产率得到cholestane-3α,5α,6β-triol 5-acetate
  参考文献：
  名称：

  1,3-Acyl migration to an epoxide. Reversible rearrangement of 5,6.beta.-epoxyepicholesteryl acetate

  摘要：

  DOI：

  10.1021/jo00166a050
• 作为产物：
  描述：

  cholestane-3α,5α,6β-triol 5-acetate 200.0 ℃ 、13.33 Pa 条件下， 反应 0.08h， 以0.68 g的产率得到5,6β-epoxy-5β-cholestan-3α-ol acetate
  参考文献：
  名称：

  1,3-Acyl migration to an epoxide. Reversible rearrangement of 5,6.beta.-epoxyepicholesteryl acetate

  摘要：

  DOI：

  10.1021/jo00166a050

文献信息

• Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds
  作者：Milan Dabović、Mira Bjelaković、Vladimir Andrejević、Ljubinka Lorenc、Mihailo Lj. Mihailović

  DOI：10.1016/s0040-4020(01)80855-3

  日期：1994.1

  induced HgO/I2 oxidation of cholest-5-en-3α-ol (6) and cholest-5-en-3β-ol (7) afforded (Scheme 3) products arising from the corresponding alkoxy radicals (12, 13 and 14a,b) and from attack of the I2O intermediate at the olefinic double bond (epoxides 15a and 16a,b respectively). With cholest-5-ene-1α,3β-diol 3-acetate (8) and cholest-7-ene-3β,5α-diol 3-acetate (9) the HgO/I2 oxidation led to unresolvable

  胆甾-5-烯-3α-醇（6）和胆甾-5-烯-3β-醇（7）的光化学诱导HgO / I 2氧化提供（方案3）相应的烷氧基自由基（12、13和14a，b）和I 2 O中间体在烯烃双键（分别为环氧化物15a和16a，b）上的侵蚀。使用胆甾5-烯-1α，3β-二醇3-乙酸盐（8）和胆甾7-烯-3β，5α-二醇3-乙酸盐（9），HgO / I 2氧化导致无法分离的复杂混合物（方案5 ）。使用相同的试剂cholest-5-en-3α-ol乙酸酯（10）和cholest-5-en-3β-ol乙酸酯（11）仅受到I 2 O的攻击，生成环氧化物20a，b，碘醇21以及重排产物19和22（方案7）（对于10而言），主要是环氧化物23a，b（方案8）的11。
• Method for synthesizing 5beta, 6beta-epoxides of steroids by a highly beta-selective epoxidation of delta5-unsaturated steroids catalyzed by ketones
  申请人：——

  公开号：US20030018188A1

  公开（公告）日：2003-01-23

  A general, efficient, and environmentally friendly method is provided for producing mostly &bgr;-epoxides of &Dgr; 5 -unsaturated steroids using certain ketones as the catalyst along with an oxidizing agent, or by using certain dioxiranes. In another aspect of the invention, a method is provided for producing mostly 5&bgr;,6&bgr;-epoxides of steroids from &Dgr; 5 -unsaturated steroids having a substituent at the 3&agr;-position by an epoxidation reaction using a ketone along with an oxidizing agent under conditions effective to generate epoxides, or using a dioxirane under conditions effective to generate epoxides. A whole range of &Dgr; 5 -unsaturated steroids, bearing different functional groups such as hydroxy, carbonyl, acetyl or ketal group as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5&bgr;,6&bgr;-epoxides with excellent &bgr;-selectivities and high yields.

  提供了一种通用、高效且环保的方法，用于利用某些酮作为催化剂以及氧化剂，或者使用某些二氧杂环丙烷，生产大部分为&Dgr; 5 -不饱和类固醇的&bgr;-环氧化物。在发明的另一个方面，提供了一种方法，通过使用酮以及氧化剂进行环氧化反应，或者在有效条件下使用二氧杂环丙烷，从3&agr;-位有取代基的&Dgr; 5 -不饱和类固醇中生产大部分为5&bgr;,6&bgr;-环氧化物。一整套带有不同官能团（如羟基、酮基、乙酰基或缩醛基）以及不同侧链的&Dgr; 5 -不饱和类固醇，方便地转化为相应的合成和生物学上有趣的5&bgr;,6&bgr;-环氧化物，具有优异的&bgr;-选择性和高产率。
• Reactions of epoxides—XXI
  作者：J.M. Coxon、M.P. Hartshorn、C.N. Muir

  DOI：10.1016/s0040-4020(01)82925-2

  日期：——

  3α-Hydroxy-5,6-epoxycholestanes gave 6-hydroxy-3α,10α-oxido-5β-methyl-19-nor compounds in addition to 6-ketones and backbone rearranged Δ13(17)-olefins on BF3-catalysed rearrangement. Similar treatment of 3α-acetoxy-5β,6β-epoxycholestane gave 5α-acetoxy-cholestane-3α,6β-diol.

  3α-羟基-5,6-环氧胆甾烷除了6-酮和在BF 3催化的骨架上重排的Δ13 （17）-烯烃外，还产生6-羟基-3α，10α-氧化-5β-甲基-19-nor化合物。。对3α-乙酰氧基-5β，6β-环氧胆甾烷进行类似处理，得到5α-乙酰氧基-胆甾烷-3α，6β-二醇。
• Method for synthesizing 5β, 6β-epoxides of steroids by a highly β-selective epoxidation of ΔΔ5-unsaturated steroids catalyzed by ketones
  申请人：Yang Dan

  公开号：US06841665B2

  公开（公告）日：2005-01-11

  A general, efficient, and environmentally friendly method is provided for producing mostly β-epoxides of Δ 5 -unsaturated steroids using certain ketones as the catalyst along with an oxidizing agent, or by using certain dioxiranes. In another aspect of the invention, a method is provided for producing mostly 5β,6β-epoxides of steroids from Δ 5 -unsaturated steroids having a substituent at the 3α-position by an epoxidation reaction using a ketone along with an oxidizing agent under conditions effective to generate epoxides, or using a dioxirane under conditions effective to generate epoxides. A whole range of Δ 5 -unsaturated steroids, bearing different functional groups such as hydroxy, carbonyl, acetyl or ketal group as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5β,6β-epoxides with excellent β-selectivities and high yields.

  本发明提供了一种通用、高效、环保的方法，使用某些酮类催化剂和氧化剂，或使用某些二氧杂环丙烷，生产大部分Δ5-不饱和类固醇的β-环氧化物。另一方面，本发明提供了一种方法，使用酮类催化剂和氧化剂，在有效条件下生成环氧化物，或使用二氧杂环丙烷，在有效条件下生成5β,6β-环氧化物，从而从3α-位置带有取代基的Δ5-不饱和类固醇中产生大部分5β,6β-环氧化物。整个Δ5-不饱和类固醇范围，带有不同的功能基团，如羟基、羰基、乙酰基或缩醛基以及不同的侧链，方便地转化为相应的合成和生物学上有趣的5β,6β-环氧化物，具有优异的β-选择性和高收率。
• Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones
  作者：Dan Yang、Guan‐Sheng Jiao

  DOI：10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#

  日期：2000.10.2

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.