3-methoxy-17-oxospiro | 157302-33-5

• 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-methoxy-17-oxospiro
• 英文别名: 3'-methoxyspiro[cyclopentane-1,16'-estra[1,3,5(10)]trien]-17'-one；3-methoxy-17-oxospiro[estra-1,3,5(10)-triene-16,1'-cyclopentane]；(8R,9S,13S,14S)-3-methoxy-13-methylspiro[6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthrene-16,1'-cyclopentane]-17-one
• CAS: 157302-33-5
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: IMXVPXCVFXLXJW-JBPLPALLSA-N

物化性质

• 沸点：
  488.2±45.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-methoxy-17-oxospiro 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以91%的产率得到(8R,9S,13S,14S,17S)-13-methylspiro[7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-16,1'-cyclopentane]-3,17-diol
  参考文献：
  名称：

  Synthesis of new 16-spirosteroids

  摘要：

  Reaction of estrone methyl ether 1 with sodium hydride and 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane, respectively, gives the 16-spirosteroid derivatives 2-4, which were reduced to the 17 beta-alcohols 7-9. Acetylation afforded the acetates 10-12. In the reaction of 1 and 1,3-dibromopropane a bis-allyl compound 5 and an annulated dihydropyran 6 were also formed. Cleavage of the ether moiety in 2 and 3 was accomplished with diisobutylaluminum hydride to give 3,17 beta-diols 13 and 14, respectively.

  DOI：

  10.1016/0039-128x(94)90118-x
• 作为产物：
  描述：

  1,4-二溴丁烷 、 3-甲氧基雌酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以84%的产率得到3-methoxy-17-oxospiro
  参考文献：
  名称：

  Synthesis of new 16-spirosteroids

  摘要：

  Reaction of estrone methyl ether 1 with sodium hydride and 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane, respectively, gives the 16-spirosteroid derivatives 2-4, which were reduced to the 17 beta-alcohols 7-9. Acetylation afforded the acetates 10-12. In the reaction of 1 and 1,3-dibromopropane a bis-allyl compound 5 and an annulated dihydropyran 6 were also formed. Cleavage of the ether moiety in 2 and 3 was accomplished with diisobutylaluminum hydride to give 3,17 beta-diols 13 and 14, respectively.

  DOI：

  10.1016/0039-128x(94)90118-x

文献信息

• Cytoprotective polycyclic compounds
  申请人：Washington Univeristy

  公开号：US20020132802A1

  公开（公告）日：2002-09-19

  The present invention is generally directed to novel enantiomeric estrogen derivatives, some of which may have one or more unsaturated bonds in conjugation with the terminal or A-ring of the structure, which have cytoprotective activity. The present invention is further directed to a process for conferring cytoprotection to a population of cells, of a subject in need thereof, involving the administration of an effective dose of the compound.

  本发明通常涉及新型对映异构体雌激素衍生物，其中一些可能具有与结构末端或A环共轭的一个或多个不饱和键，具有细胞保护活性。本发明进一步涉及一种为需要细胞保护的受试者的细胞群体赋予细胞保护的过程，包括给予化合物的有效剂量。
• Synthesis of new 16-spirosteroids
  作者：Lutz F. Tietze、János Wölfling、Gyula Schneider、Mathias Noltemeyer

  DOI：10.1016/0039-128x(94)90118-x

  日期：1994.5

  Reaction of estrone methyl ether 1 with sodium hydride and 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane, respectively, gives the 16-spirosteroid derivatives 2-4, which were reduced to the 17 beta-alcohols 7-9. Acetylation afforded the acetates 10-12. In the reaction of 1 and 1,3-dibromopropane a bis-allyl compound 5 and an annulated dihydropyran 6 were also formed. Cleavage of the ether moiety in 2 and 3 was accomplished with diisobutylaluminum hydride to give 3,17 beta-diols 13 and 14, respectively.