2β,3β-dihydroxy-5α-cholestane | 10146-89-1

• 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: 2β,3β-dihydroxy-5α-cholestane
• 英文别名: 5α-cholestane-2β, 3β-diol；5α-cholestane-2β,3β-diol；5α-Cholestan-2β,3β-diol；cholestane-2β,3β-diol；(10S)-2c.3c-Dihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；2β.3β-Dihydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；Cholestane-2,3-diol, (2beta,3beta,5alpha)-；(2S,3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-2,3-diol
• CAS: 10146-89-1
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: NWQBDOPDVUJEGJ-DDLCNDOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2β,3β-dihydroxy-5α-cholestane 在 3 A molecular sieve 、 焦磷酸硫胺素 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 15.0h， 以32%的产率得到5-Alpha-胆甾烷-3-酮
  参考文献：
  名称：

  Reaktionen mit phosphororganischen Verbindungen, 48. Mitt.

  摘要：

  DOI：

  10.1007/bf00905072
• 作为产物：
  描述：

  2β-acetoxy-5α-cholestan-3β-ol 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以90 mg的产率得到2β,3β-dihydroxy-5α-cholestane
  参考文献：
  名称：

  Syntheses of Steroidaltrans-Iodo Acetates

  摘要：

  下列甾体烯烃与乙酸中的碘-醋酸铜（II）反应，可得到相应的甾体反式碘醋酸酯：5α-胆甾烯-1-、-2-和-3-烯；以及 5β-胆甾烯-1-、-2-和-3-烯：5α-胆甾烯-1-、-2-和-3-烯；以及 5β-胆甾烯-1-、-2-和-3-烯。

  DOI：

  10.1246/bcsj.60.426

文献信息

• Regioselective enzymatic acylation of vicinal diols of steroids
  作者：M. Manuel Cruz Silva、Sergio Riva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2005.01.104

  日期：2005.3

  Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.

  完整的甾族化合物的2，3-和3，4-邻位二醇的单酰化衍生物是通过区域选择性脂肪酶催化的酯交换反应制备的。取决于羟基的构型，酶对邻二醇具有不同的选择性。
• A New Ready, High-Yielding, General Procedure for Acetalization of Carbonyl Compounds
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo

  DOI：10.1055/s-1987-27955

  日期：——

  Carbonyl compounds are smoothly and rapidly acetalized by treatment with alcohols, in anhydrous acetonitrile, in the presence of polystyryl diphenyl phosphine - iodine complex as catalyst. Open and cyclic acetals, including 1,3-dioxolanes, 1,3-oxathiolanes, and 1,3-dithiolanes, of miscellaneous aldehydes and ketones have been successfully prepared in this way. The isolation of the product is very easily performed, by simple filtration of the polymer-linked phosphine oxide which is formed in the reaction.

  通过使用醇类、无水乙腈中，在聚苯乙烯二苯基膦-碘复合物作为催化剂的条件下，羰基化合物可以顺利且快速地进行缩醛化反应。多种醛和酮的开链型和环状缩醛，包括1,3-二氧戊环、1,3-氧硫环戊烷和1,3-二硫环戊烷，都已成功通过这种方式制备。产品很容易通过简单过滤反应中形成的聚合物连接的磷氧化物来分离。
• A New Synthesis of<i>cis</i>-Diol from Alkene Using Iodine-Ammonium Cerium(IV) Nitrate
  作者：C. Akira Horiuchi、Gong Dan、Masaki Sakamoto、Kazuhiko Suda、Shigeru Usui、Okihiko Sakamoto、Shinya Kitoh、Satoshi Watanabe、Takamitsu Utsukihara、Sukekatsu Nozaki

  DOI：10.1055/s-2005-916040

  日期：——

  The reaction mixtures of 5α-cholest-2-ene with iodine-ammonium cerium(IV) nitrate [CAN(IV)] were converted with potassium hydroxide in methanol-water to give the more hindered 2β,3β-diol in high yield. Cyclohexene and cycloheptene similarly reacted to the corresponding cis-diols in good yield. It was found that this reaction intermediate proceeds to give trans-iodoacetate via trans-iodonitrate. This new synthetic method provided several advantages over the Prevost reaction.

  5α-胆甾-2-烯与碘化铵硝酸铈(IV)[CAN(IV)]的反应混合物在甲醇-水溶液中用氢氧化钾处理，以高产率得到空间位阻较大的2β,3β-二醇。环己烯和环庚烯也以优良产率生成相应的顺式-二醇。研究发现，该反应中间体通过反式-碘硝酸盐生成反式-碘乙酸盐。这种新的合成方法相比于Prevost反应具有若干优势。
• A New Synthesis of<i>cis</i>-Diol from Olefin Using Iodine-Copper(II) Acetate
  作者：C. Akira Horiuchi、J. Yasuo Satoh

  DOI：10.1246/cl.1988.1209

  日期：1988.7.5

  The reaction mixtures of 5α-cholest-2-ene with iodine and copper(II) acetate were converted with potassium hydroxide in methanol-water to give the more hindered 2β, 3β-diol in high yield. Cyclohexene and cycloheptene similarly gave the corresponding cis-diols in good yield. This new synthetic method afforded several advantage over the Prevost reaction.

  5α-cholest-2-ene 与碘和乙酸铜 (II) 的反应混合物在甲醇-水中用氢氧化钾转化，以高产率得到受阻更多的 2β, 3β-二醇。环己烯和环庚烯同样以良好的产率得到相应的顺式二醇。与 Prevost 反应相比，这种新的合成方法具有多项优势。
• DISTRIBUTION OF <i>BEMISIA TABACI</i> (HEMIPTERA: ALEYRODIDAE) BIOTYPES IN ITALY
  作者：Stefano Demichelis、Domenico Bosco、Aulo Manino、Daniele Marian、Piero Caciagli

  DOI：10.4039/ent132519-4

  日期：2000.8

  Esterase banding patterns in native polyacrylamide gel electrophoresis, squash silver leaf (SSL) induction, and tomato yellow leaf curl begomovirus-Sardinia (TYLCV-Sar) transmission capability were investigated to evaluate variations among populations of Bemisia tabaci (Gennadius) from Italy and to relate their distribution to their geographic origin. Adults of the B biotype, adults of the Q-like biotype (which is similar to a Spanish biotype), and adults without esterase bands were found. The B biotype has been found in Italy since 1989. Two populations, including mainly B and Q-like biotypes, showed similar TYLCV-Sar transmission efficiency, independent of esterase banding pattern. Only populations from Liguria and Sardinia, which contained almost exclusively B-biotype individuals, were able to induce SSL. We observed that adults of the B biotype are widespread in greenhouses of northern Italy and Sardinia, whereas those of the Q-like biotype are present only in fields of southern Italy. These results suggest that the B biotype of B. tabaci was introduced into Italy likely while trading ornamental plants, whereas the Q-like biotype is native to the Mediterranean region.

  摘要 研究了原生聚丙烯酰胺凝胶电泳中的酯酶条带模式、南瓜银叶（SSL）诱导和番茄黄卷叶病begomovirus-撒丁岛（TYLCV-Sar）传播能力，以评估来自意大利的Bemisia tabaci（Gennadius）种群之间的差异，并将其分布与其地理起源联系起来。研究发现了 B 型生物型成虫、Q 型生物型成虫（类似于西班牙生物型）和无酯酶带的成虫。B 生物型自 1989 年起在意大利发现。两个种群（主要包括 B 型和 Q 型生物型）显示出相似的 TYLCV-Sar 传播效率，与酯酶条带模式无关。只有来自利古里亚（Liguria）和撒丁岛（Sardinia）的种群能够诱发 SSL，这两个种群几乎只包含 B 型生物型个体。我们观察到，B 生物型的成虫广泛存在于意大利北部和撒丁岛的温室中，而 Q 型生物型的成虫只存在于意大利南部的田野中。这些结果表明，B. tabaci 的 B 型生物型很可能是在观赏植物贸易中引入意大利的，而 Q 型生物型则是地中海地区的原生生物。