(+/-)-16-(((tert-butyl)diphenylsilyl)oxy)-3-methoxy-14β-methylgona-1,3,5(10),9(11),16-pentaen-15-one | 135586-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (+/-)-16-(((tert-butyl)diphenylsilyl)oxy)-3-methoxy-14β-methylgona-1,3,5(10),9(11),16-pentaen-15-one
• CAS: 135586-92-4
• 化学式: C₃₅H₃₈O₃Si
• 分子量: 534.77
• InChiKey: QAVFJSJXZBYCPB-VKHSVWCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  7-甲氧基-4-乙烯基-1,2-二氢萘 、 1-Methylcyclopent-1-en-3,4-dione 生成 (+/-)-16-(((tert-butyl)diphenylsilyl)oxy)-3-methoxy-14β-methylgona-1,3,5(10),9(11),16-pentaen-15-one
  参考文献：
  名称：

  E. Dane's route to estrone revisited

  摘要：

  The chirogenic Diels/Alder reactions of the general pattern AB + D --> ABCD, (i): 2 + 3 --> rac-8a (major) + rac-9a (minor) (85%), (ii): 2 + 10a --> rac-11a (89%), and (iii): 2 + 10b --> rac-11b (90%), now have been accomplished in the presence of Lewis acid, (i): BF3.OEt2, (ii) or (iii): TiCl4. Case (iii) may be used as the initial move towards (+/-)-norgestrel (rac-14).

  DOI：

  10.1016/s0040-4039(00)92705-9

文献信息

• Total Synthesis with a Chirogenic Opening Move Demonstrated on Steroids with Estrane or 18a-Homoestrane Skeleton
  作者：Gerhard Quinkert、Michael Del Grosso、Astrid Döring、Wolfgang Döring、Ralf I. Schenkel、Markus Bauch、Gernot T. Dambacher、Jan W. Bats、Gottfried Zimmermann、Gerd Dürner

  DOI：10.1002/hlca.19950780524

  日期：1995.8.9

  A concept of first choice for the synthesis of the title compounds had been proposed by Dane in the late 1930s. It was soon turned down, because the opening move–a chirogenic Diels-Alder reaction – did not work. With Lewis acids as mediators, however, a successful start has been achieved now. With Ti complexes of chelating ligands (Seebach's TADDOLs (= α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanols))

  Dane在1930年代后期提出了合成标题化合物的首选方法。很快就被拒绝了，因为开场动作–致色Diels - Alder反应–无效。但是，以路易斯酸为介质，现在已经取得了成功的开始。使用螯合配体的Ti络合物（Seebach 's TADDOLs（=α，α，α'，α'-四芳基-1,3-二氧戊环-4,5-二甲醇）），确实发生了所需加合物的对映选择性形成。已经完成了2和3a的有效总合成。