17β-hydroxyandrost-5-en-3-one 3,3-ethylene acetal | 96191-80-9

• 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: 17β-hydroxyandrost-5-en-3-one 3,3-ethylene acetal
• 英文别名: (8R,9S,10R,13S,14S)-10,13-dimethylspiro[1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-ol
• CAS: 96191-80-9
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: QIOYEDVDPAWRGZ-BLRAIOBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-hydroxyandrost-5-en-3-one 3,3-ethylene acetal 在 四氢噻喃-4-酮 1,1-二氧化物 Oxone 、 edetate disodium 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#
• 作为产物：
  描述：

  雄甾-5-烯-17-酮-3-乙烯缩酮 在 丙基氯化镁 作用下， 以65%的产率得到17β-hydroxyandrost-5-en-3-one 3,3-ethylene acetal
  参考文献：
  名称：

  在氯化铈（III）存在下，将烷基格氏试剂高效亲核加成到17-酮类固醇上：雄激素受体拮抗剂17α-丙基-17β-羟基-4-androsten-3-one的合成

  摘要：

  无水氯化铈（III）显着增强了将烷基格氏试剂添加到位阻17-酮类固醇中，并显着抑制了异常反应，同时获得的加成产物具有良好或优异的收率和较高的立体选择性。

  DOI：

  10.1016/0040-4039(94)88011-5

文献信息

• 12,13-Epoxy-<i>C</i>-nor-<i>D</i>-homosteroids. VIH. Transformation of 12α,13α-Epoxyetiojerv-5-ene-3,17-dione 3,3-Ethylene Acetal into Testosterone
  作者：Akio Murai、Noriaki Iwasa、Tadashi Masamune

  DOI：10.1246/bcsj.53.259

  日期：1980.1

  Transformation of the title epoxy ketone (2) into testosterone (1), which implies synthesis of the hormone 1 from jervine, is described. Irradiation of 2 by a low-pressure lamp in dioxane afforded an androstane-12,17-dione derivative, which was reduced regioselectively with lithium tri-t-butoxyaluminium hydride to give 12β-hydroxy ketone (5). The compound 5 was transformed via a. four-step process into androstan-4-ene-3,17-dione, which was converted into 1 by a known procedure. The overall yield amounted to 1.8% from jervine.

  描述了标题环氧酮 (2) 转化为睾酮 (1)，这意味着从杰文合成激素 1。在二恶烷中用低压灯照射 2，得到雄甾烷-12,17-二酮衍生物，用三叔丁氧基氢化铝锂进行区域选择性还原，得到 12β-羟基酮 (5)。化合物5通过a转化。生成雄甾烷-4-烯-3,17-二酮的四步法，通过已知程序将其转化为1。 jervine 的总产率为 1.8%。
• 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.
• Highly efficient nucleophilic addition of alkyl Grignard reagents to 17-ketosteroids in the presence of cerium(III) chloride: Synthesis of 17α-propyl-17β-hydroxy-4-androsten-3-one, an androgen receptor antagonist
  作者：Xun Li、Shankar M. Singh、Fernand Labrie

  DOI：10.1016/0040-4039(94)88011-5

  日期：1994.2

  The addition of alkyl Grignard reagents to sterically hindered 17-ketosteroids was significantly enhanced by anhydrous cerium(III) chloride with notable suppression of abnormal reactions, while the addition products were obtained in good to excellent yields and high stereoselectivity.

  无水氯化铈（III）显着增强了将烷基格氏试剂添加到位阻17-酮类固醇中，并显着抑制了异常反应，同时获得的加成产物具有良好或优异的收率和较高的立体选择性。