(8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene | 213337-06-5

• 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: (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene
• 英文别名: (8S,9S,13S,14S)-17-ethenyl-13-methyl-3-phenylmethoxy-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthrene
• CAS: 213337-06-5
• 化学式: C₂₇H₃₀O
• 分子量: 370.535
• InChiKey: UPNBJHTYIJOZEF-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene 在 四氟硼酸-二乙醚络合物 、 氢氧化钾 、 Ru(CO)H(Cl)(tri(cyclohexyl)phosphine)₃ 、 双氧水 、 烯丙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 33.0h， 生成 (20S)-3-benzyloxy-19,26(27)-dinorchola-1,3,5(10),16,23E-pentaen-25-oic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Ruthenium-Catalyzed Hydrovinylation of 1,3-Dienes:  Application to the Generation of a 20(S) Steroidal Side Chain

  摘要：

  The addition of ethylene to 1,3-dienes and 1-vinylcycloalkenes, catalyzed by two ruthenium complexes, proceeds in a regioselective fashion to afford 3-methyl-1,4-dienes as products. For a steroidal-based 1-vinylcycloalkene, the addition is stereospecific, giving a product with a 20(S) configuration.

  DOI：

  10.1021/ol030031+
• 作为产物：
  描述：

  3-O-苄基雌酮 在 四(三苯基膦)钯 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  Design and Synthesis of Estrarubicin: a Novel Class of Estrogen-Anthracenedione Hybrids

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199809)1998:9<1965::aid-ejoc1965>3.0.co;2-s

文献信息

• Ligand Tuning in Asymmetric Hydrovinylation of 1,3-Dienes: A Stereoselective Route to Either Steroid-C₂₀ (<i>S</i>) or -C₂₀ (<i>R</i>) Derivatives
  作者：Biswajit Saha、Craig R. Smith、T. V. RajanBabu

  DOI：10.1021/ja711475f

  日期：2008.7.1

  1,3-Dienes derived from steroidal D-ring C(17)-ketones undergo Ni(II)-catalyzed hydrovinylation to give 1,2- or 1,4-addition of ethylene. Using finely tuned phosphoramidite ligands, it is possible to synthesize either the C(20) (R)- or (S)-derivatives without mutual contamination. The proportion of the 1,4-adduct, which is also formed stereoselectively, can be minimized by optimizing the reaction conditions. Because the two alkenes in the resultant dienes have differing steric demands for many potential reactions, and are ideally juxtaposed for further D-ring functionalization, these intermediates could be useful for the preparation of biologically important compounds such as vitamin D analogs and various antitumor steroidal glycosides.
• Design and Synthesis of Estrarubicin: a Novel Class of Estrogen-Anthracenedione Hybrids
  作者：Francesco De Riccardis、Daniela Meo、Irene Izzo、Marcello Di Filippo、Agostino Casapullo

  DOI：10.1002/(sici)1099-0690(199809)1998:9<1965::aid-ejoc1965>3.0.co;2-s

  日期：1998.9
• Regio- and Stereoselective Ruthenium-Catalyzed Hydrovinylation of 1,3-Dienes:  Application to the Generation of a 20(<i>S</i>) Steroidal Side Chain
  作者：Zhengjie He、Chae S. Yi、William A. Donaldson

  DOI：10.1021/ol030031+

  日期：2003.5.1

  The addition of ethylene to 1,3-dienes and 1-vinylcycloalkenes, catalyzed by two ruthenium complexes, proceeds in a regioselective fashion to afford 3-methyl-1,4-dienes as products. For a steroidal-based 1-vinylcycloalkene, the addition is stereospecific, giving a product with a 20(S) configuration.