17-oxa-5α-androstan-3-one | 83625-97-2

• 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: 17-oxa-5α-androstan-3-one
• 英文别名: (3aS,3bR,5aS,9aS,9bS,11aS)-9a,11a-dimethyl-3,3a,3b,4,5,5a,6,8,9,9b,10,11-dodecahydro-2H-naphtho[2,1-e][1]benzofuran-7-one
• CAS: 83625-97-2
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: URQXFSXJCPWHIX-PZAYZMLXSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17-oxa-5α-androstan-3-one 在 吡啶 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 97.0h， 生成 3-selena-17-oxa-5α-androstane
  参考文献：
  名称：

  Transformation of epiandrosterone into 3-oxa-, 3-thia-, 3-selena-, and 3-aza-17-oxaandrostanes of the 5α series based on β-scission of alkoxyl radicals

  摘要：

  3-beta-Hydroxy-5-alpha-androstan-17-one was transformed into 17-oxa-5-alpha-androstan-3-beta-ol in five steps involving conversion of the 17-ketone via the corresponding lactol to its hypoiodite and thence a regioselective beta-scission under irradiation to give ring D seco iodoformate, from which the 17-oxasteroids were derived. Four bisheterosteroids 3,17-dioxa-5-alpha-androstane, 3-thia-17-oxa-5-alpha-androstane, 3-aza-17-oxa-5-alpha-androstane, and 3-selena-17-oxa-5-alpha-androstane) were synthesized from 17-oxa-5-alpha-androstan-3-beta-ol via 5, 8, 8, and 9 steps, respectively, involving a second regioselective beta-scission of an alkoxyl radical as the key step.

  DOI：

  10.1016/0039-128x(90)90059-k
• 作为产物：
  描述：

  3-乙酰基-5Α-雄烷二醇 在 chromium(VI) oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 碘 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 苯 为溶剂， 反应 5.5h， 生成 17-oxa-5α-androstan-3-one
  参考文献：
  名称：

  INSERTION OF OXYGEN ATOM IN STEROID FRAMEWORKS–A NEW METHOD OF TRANSFORMATION OF HYDROXYSTEROID INTO OXASTEROID

  摘要：

  描述了饱和羟基甾体化合物向甾体酮的二步转化过程；该反应涉及羟基甾体化合物的次碘酸盐在氧化汞（II）和碘的作用下进行光反应，生成异构的甲酰酯（例如，2和3），这些甲酰酯通过用硼氢化钠环化形成甾体酮（例如，4和5）。

  DOI：

  10.1246/cl.1982.1233

文献信息

• Photoinduced transformations. Part 73. Transformations of five- (and six-) membered cyclic alcohols into five- (and six-) membered cyclic ethers - a new method of a two-step transformation of hydroxy steroids into oxasteroids
  作者：Hiroshi Suginome、Shinji Yamada

  DOI：10.1021/jo00194a015

  日期：1984.10
• INSERTION OF OXYGEN ATOM IN STEROID FRAMEWORKS–A NEW METHOD OF TRANSFORMATION OF HYDROXYSTEROID INTO OXASTEROID
  作者：Hiroshi Suginome、Shinji Yamada

  DOI：10.1246/cl.1982.1233

  日期：1982.8.5

  A two-step transformation of saturated hydroxysteroids into oxasteroids is described; the reaction involves photo-reaction of the hypoiodites of the hydroxysteroids generated with mercury(II) oxide and iodine to give isomeric formyl esters [e.g., 2 and 3], which are cyclized to oxasteroids [e.g.,4 and 5] with sodium borohydride.

  描述了饱和羟基甾体化合物向甾体酮的二步转化过程；该反应涉及羟基甾体化合物的次碘酸盐在氧化汞（II）和碘的作用下进行光反应，生成异构的甲酰酯（例如，2和3），这些甲酰酯通过用硼氢化钠环化形成甾体酮（例如，4和5）。
• Transformation of epiandrosterone into 3-oxa-, 3-thia-, 3-selena-, and 3-aza-17-oxaandrostanes of the 5α series based on β-scission of alkoxyl radicals
  作者：Hiroshi Suginome、Jian Bo Wang

  DOI：10.1016/0039-128x(90)90059-k

  日期：1990.8

  3-beta-Hydroxy-5-alpha-androstan-17-one was transformed into 17-oxa-5-alpha-androstan-3-beta-ol in five steps involving conversion of the 17-ketone via the corresponding lactol to its hypoiodite and thence a regioselective beta-scission under irradiation to give ring D seco iodoformate, from which the 17-oxasteroids were derived. Four bisheterosteroids 3,17-dioxa-5-alpha-androstane, 3-thia-17-oxa-5-alpha-androstane, 3-aza-17-oxa-5-alpha-androstane, and 3-selena-17-oxa-5-alpha-androstane) were synthesized from 17-oxa-5-alpha-androstan-3-beta-ol via 5, 8, 8, and 9 steps, respectively, involving a second regioselective beta-scission of an alkoxyl radical as the key step.