2α-bromo-5α-cholestan-3-one | 1452-34-2

• 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: 2α-bromo-5α-cholestan-3-one
• 英文别名: 2alpha-Bromo-5alpha-cholestan-3-one；(2R,5S,8R,9S,10S,13R,14S,17R)-2-bromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1452-34-2
• 化学式: C₂₇H₄₅BrO
• 分子量: 465.558
• InChiKey: DHZKAQAKUFROMZ-RRFIWRICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2α-bromo-5α-cholestan-3-one 在 水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以62%的产率得到2-hydroxycholestan-3-one
  参考文献：
  名称：

  Addressable Cholesterol Analogs for Live Imaging of Cellular Membranes

  摘要：

  Cholesterol is an essential component of most biological membranes and serves important functions in controlling membrane integrity, organization, and signaling. However, probes to follow the dynamic distribution of cholesterol in live cells are scarce and so far show only limited applicability. Herein, we addressed this problem by synthesizing and characterizing a class of versatile and clickable cholesterol-based imidazolium salts. We show that these cholesterol analogs faithfully mimic the biophysical properties of natural cholesterol in phospholipid mono- and bilayers, and that they integrate into the plasma membrane of cultured and primary human cells. The membrane-incorporated cholesterol analogs can be specifically labeled by click chemistry and visualized in live-cell imaging experiments that show a distribution and behavior comparable with that of endogenous membrane cholesterol. These results indicate that the cholesterol analogs can be used to reveal the dynamic distribution of cholesterol in live cells.

  DOI：

  10.1016/j.chembiol.2018.04.015
• 作为产物：
  描述：

  3β-胆甾烷醇 在 氢溴酸 、 溴 、 三氧化硫吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 2α-bromo-5α-cholestan-3-one
  参考文献：
  名称：

  Ruthenium nanoparticles ligated by cholesterol-derived NHCs and their application in the hydrogenation of arenes

  摘要：

  我们在这里展示了由胆固醇衍生的两个刚性NHC配体稳定的钌纳米颗粒（Ru-NPs）。

  DOI：

  10.1039/c8cc02833h

文献信息

• Rhodium(I)-Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones
  作者：Tianwen Sun、Yuna Zhang、Bo Qiu、Yafei Wang、Yuting Qin、Guangbin Dong、Tao Xu

  DOI：10.1002/anie.201713179

  日期：2018.3.5

  Described here is the first example of a rhodium‐catalyzed carboacylation/aromatization cascade of a C=O bond by C−C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and adds across a C=O bond with subsequent elimination, thus providing a unique strategy to access a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained

  这里描述的是第一个通过CC活化的C = O键的铑催化的碳酰化/芳香化级联反应的第一个例子。在这种转化中，反应性的若丹丹酮络合物是区域选择性生成的，并通过一个C = O键加成并随后被消除，从而提供了一种独特的策略来接近多取代的苯并呋喃支架。以高收率获得了多种苯并呋喃类似物。机理研究表明，三环内酯是可行的中间体。将该方法应用于C13-deOH-乙烯基呋喃呋喃和C13-deOH-二氢吲哚酮G的全合成。
• Dehalogenation of α -haloketones and -dibromides with nickel boride
  作者：JC Sarma、M Borbaruah、R.P. Sharma

  DOI：10.1016/s0040-4039(00)98778-1

  日期：1985.1

  α-Haloketones and -dibromides are converted to the corresponding ketones and alkenes respectively with nickel boride generated from sodium borohydride and nickel chloride.

  α-卤代酮和-二溴化物分别与由硼氢化钠和氯化镍生成的硼化镍分别转化为相应的酮和烯烃。
• A New<b><i>α</i></b>-Iodination of Ketones Using Iodine-Ammonium Cerium(IV) Nitrate in Alcohol or Acetic Acid
  作者：C. Akira Horiuchi、Shinji Kiji

  DOI：10.1246/bcsj.70.421

  日期：1997.2

  The direct α-iodination of various ketones using iodine-ammonium cerium(IV) nitrate in acetic acid or alcohol gave the corresponding α-iodo ketones in high yields. The effect of cerium salt on the iodination of ketones, and the iodination of 5α-cholestan-3-one using several methods are also discussed. In the reaction of 3,3,5-trimethylcyclohexanone and unsymmetrical ketones, such as 2-hexanone and

  在乙酸或酒精中使用碘铵铈 (IV) 对各种酮进行直接 α-碘化，以高产率得到相应的 α-碘酮。还讨论了铈盐对酮碘化的影响，以及使用几种方法碘化5α-cholestan-3-one。3,3,5-三甲基环己酮与2-己酮、2-庚酮等不对称酮在甲醇、乙醇、1-丙醇、2-丙醇的作用下反应，得到区域选择性碘化产物。在溴化的情况下，酮与溴和硝酸铈 (IV) 铵的反应也产生相应的 α-溴酮。
• Process for the preparation of androstane-3,17-dione derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04097334A1

  公开（公告）日：1978-06-27

  A process for the preparation of androstane-3,17-dione compounds of the formula ##STR1## wherein X is 1,2-methylene or 1- or 2-methyl, comprises fermenting a sterol of the formula ##STR2## wherein X is as above and R.sub.1 is the hydrocarbon residue of 8-10 carbon atoms, of a sterol, with a microorganism culture capable of effecting the side chain degradation of sterols.

  一种制备雄烷-3,17-二酮化合物的方法，其化学式为##STR1##其中X为1,2-亚甲基或1-或2-甲基，包括利用一种能够使甾醇的侧链降解的微生物培养物发酵具有化学式##STR2##其中X如上所述，R.sub.1为8-10个碳原子的烃残基的甾醇。
• Efficient synthesis of novel A-ring-substituted 1,2,3-triazolylcholestane derivatives via catalytic azide-alkyne cycloaddition
  作者：Zalán Kádár、Éva Frank、Gyula Schneider、Judit Molnár、István Zupkó、János Kóti、Bruno Schönecker、János Wölfling

  DOI：10.3998/ark.5550190.0013.320

  日期：——

  reported for the formation of novel 2αtriazolylcholestane derivatives. The scheme involves transformation of the starting cholestanone to the corresponding azido compound and efficient conversions of 2α-azido-5α-cholestan-3-one (3) with various terminal alkynes through use of the ‘click’ chemistry approach. Finally, the oxo group of these heterocyclic steroidal derivatives was reduced, and the resultant

  报道了一种简单方便的合成路线，用于形成新型 2α三唑基胆甾烷衍生物。该方案涉及将起始胆甾酮转化为相应的叠氮化合物，并通过使用“点击”化学方法将 2α-azido-5α-cholestan-3-one (3) 与各种末端炔烃有效转化。最后，还原这些杂环甾族衍生物的氧代基团，并分离得到的差向异构三唑醇混合物。筛选了合成的 2triazolyl-3-ketones 对三种人类癌细胞系的抗增殖活性。然而，只有少数测试化合物发挥了适度的细胞生长抑制作用。