3-oxo-4-oxa-5α-androstanone | 59251-75-1

• 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: 3-oxo-4-oxa-5α-androstanone
• 英文别名: 4-Oxa-5α-androstan-3,17-dion；4-Oxa-5alpha-androstane-3,17-dione；(3aS,3bR,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydroindeno[5,4-f]chromene-1,7-dione
• CAS: 59251-75-1
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: MXDPQMQGOXWUBC-GEDVFAKWSA-N

物化性质

• 沸点：
  442.7±45.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-oxo-4-oxa-5α-androstanone 在 盐酸 作用下， 生成 methyl 3-[(3aS,5aS,6S,9aR,9bS)-3a,6-dimethyl-3-oxo-1,2,4,5,5a,9,9a,9b-octahydrocyclopenta[a]naphthalen-6-yl]propanoate
  参考文献：
  名称：

  Secoandrostansäurenal对映体前列腺素类似物-II：6-戊基-4-nor-3,5-seco-androstan-3-säuren

  摘要：

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。

  DOI：

  10.1016/0040-4020(75)80159-1
• 作为产物：
  描述：

  4-去甲-3,5-开环-5,17-二氧代雄甾烷-3-酸 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 oxonium 作用下， 以 乙醇 为溶剂， 生成 3-oxo-4-oxa-5α-androstanone
  参考文献：
  名称：

  Is the magnetic shielding effect of a lactone group the simple sum of those of a ketone and an ether?

  摘要：

  3-Oxo-4-oxa-5 alpha-androstanone (1) was synthesized in order to obtain the NMR shielding parameters for lactone group. The assignment of H-1-NMR and substituent-induced shifts (SIS) from the corresponding androstanone (2) are presented. A simple sum of the magnetic shieldings of ketone and ether can satisfactorily reproduce the observed SIS values due to the lactone group of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00580-8

文献信息

• Secoandrostansäuren als enantiomere prostaglandin-analoga—II
  作者：M. Baumgarth、K. Irmscher

  DOI：10.1016/0040-4020(75)80159-1

  日期：1975.1

  A synthesis of the enantiomeric tetrahydro-PGA1 analogue 48 is described. In addition the homoacid 50, its pentanor analogue 39 and its epimer 51, the 6-deoxy compounds 13 and 16 as well as the lactones 14, 53, 56 and 68 were prepared as compounds closely related to 48. Simple androstane derivatives served as starting materials for the syntheses. Key intermediates were 4, 32 and 63.

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。
• Is the magnetic shielding effect of a lactone group the simple sum of those of a ketone and an ether?
  作者：Yoshimasa Fukazawa、Takeharu Haino、Yoshiaki Kondoh

  DOI：10.1016/s0040-4039(99)00580-8

  日期：1999.4

  3-Oxo-4-oxa-5 alpha-androstanone (1) was synthesized in order to obtain the NMR shielding parameters for lactone group. The assignment of H-1-NMR and substituent-induced shifts (SIS) from the corresponding androstanone (2) are presented. A simple sum of the magnetic shieldings of ketone and ether can satisfactorily reproduce the observed SIS values due to the lactone group of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.