23-oxotigogenin acetate | 28404-65-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 23-oxotigogenin acetate
• 英文别名: [(1R,2S,4S,5'R,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-3'-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] acetate
• CAS: 28404-65-1
• 化学式: C₂₉H₄₄O₅
• 分子量: 472.665
• InChiKey: TUJVKSOFWMFECQ-KBCBJNRVSA-N

物化性质

• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  23-oxotigogenin acetate 在 lithium aluminium tetrahydride 、 碘苯二乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.75h， 生成 (22S,23S,24R)-23-hydroxymethyl-16,22:22,25-diepoxy-26,27-dinor-5α-cholestan-3β-ol
  参考文献：
  名称：

  二乙酰氧基碘苯介导合成源自薯蓣皂甙元和替加皂甙元的非天然呋喃螺甾烷皂甙元

  摘要：

  两种带有呋喃螺甾烷侧链的非天然类固醇皂甙是从容易获得的螺甾烷皂甙元、tigogenin 和薯蓣皂甙元开始制备的，合成方案包括：（i）在 C-23 位引入羰基，（ii）二乙酰氧基碘苯诱导的 F -环收缩和 (iii) LiAlH4 还原新出现的甲氧基羰基部分。新化合物的结构由核磁共振和 X 射线研究证实。

  DOI：

  10.1016/j.steroids.2013.05.013
• 作为产物：
  描述：

  23α,24-epoxytigogenin acetate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以21%的产率得到23-oxotigogenin acetate
  参考文献：
  名称：

  On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids

  摘要：

  The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products-the isometric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were also obtained upon treatment of 23,24-epoxysapogenins with BF3. The epoxides treated with TiCl4 afforded mostly chlorohydrins and no rearranged products were detected. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.02.010

文献信息

• On reactions of spirostane sapogenins with benzeneseleninic anhydride
  作者：Izabella Jastrzębska、Aneta Dobrogowska、Ewa Lutostańska、Jacek W. Morzycki

  DOI：10.1016/j.tet.2010.05.013

  日期：2010.7

  Direct dehydrogenation of spirostane sapogenins with benzeneseleninic anhydride/iodoxybenzene afforded the Δ22 derivatives in low yields. The reactions catalyzed by BF3/Et2O produced the 23-oxo-sapogenins in addition to their 22-oxo-23-spiro-isomers. The reactions of sapogenins with benzeneseleninic anhydride carried out in the presence of TiCl4 afforded products chlorinated at C23.

  与spirostane皂角苷配基的直接脱氢苯亚硒酸酐/ iodoxybenzene得到Δ 22在低的产率的衍生物。BF 3 / Et 2 O催化的反应除了生成22-oxo-23-spiro异构体外，还生成了23-oxo-sapogenins。皂苷元与苯硒二酸酐的反应在TiCl 4的存在下进行，得到在C23氯化的产物。
• Lewis acid-mediated isomerisation of (25R)-3β-acetoxy-5α-spirostan-23-one, a C-22 spiroacetal: an approach to the synthesis of C-23 spiroacetal steroidal sapogenins
  作者：Rosendo Hernández、José J. Marrero-Tellado、Keith Prout、Ernesto Suáez

  DOI：10.1039/c39920000275

  日期：——

  Treatment of (25R)-3β-acetoxy-5α-spirostan-23-one (23-oxo-tigogenin acetate)3 with titanium tetrachloride afforded the 22-oxo-23-spiroacetal isomer 4 in excellent yield.

  用四氯化钛处理（25 R）-3β-乙酰氧基-5α-螺氧杂环丁烷-23-一（23-氧代-蛇毒苷原乙酸酯）3，以优异的收率得到22-氧代-23-螺缩醛异构体4。
• Photoinduced Isomerization of 23-Oxosapogenins: Conformational Analysis and Spectroscopic Characterization of 22-Isosapogenins
  作者：Izabella Jastrzębska、Marcin Górecki、Jadwiga Frelek、Rosa Santillan、Leszek Siergiejczyk、Jacek W. Morzycki

  DOI：10.1021/jo3022549

  日期：2012.12.21

  The first synthesis of 22-isospirostane derivatives is described. They were obtained by photochemical isomerization of 23-oxosapogenins. The structure of 23-oxo-22-isotigogenin acetate (12) was proved by a single crystal X-ray diffraction, while structures of 23-oxo-22-isodiosgenin acetate (13) and 23-oxo-22-isosarsasapogenin acetate (14) were elucidated by spectroscopic methods. 22-Isodiosgenin acetate (17) was obtained by NaBH4 reduction of the 23-oxo derivative 13 followed by the two-step Barton-McCombie deoxygenation procedure. Conformational analysis of 22-iso compounds was carried out with CD and NMR, as well as DFT calculations.
• 903. The stereochemistry of the side-chain of the steroidal sapogenins : configuration at C(22) of normal and iso-sapogenins
  作者：R. K. Callow、P. N. Massy-Beresford

  DOI：10.1039/jr9570004482

  日期：——
• The synthesis and antifungal activity of (20 S )-3β-acetoxy-5α-pregnane-20,16β-carbolactone against fluconazole – Resistant Candida cells
  作者：Izabella Jastrzebska、Katarzyna Niemirowicz、Wioleta I. Brzozowska、Robert Bucki

  DOI：10.1016/j.steroids.2016.12.009

  日期：2017.2

  An efficient procedure for the synthesis of (20S)-3 beta-acetoxy-511-pregnane-20,16 beta-carbolactone is described. Bactericidal and fungicidal activity of the lactone against different bacteria such as MSSA, MESA, E. coli ESBL, P. aeruginosa and clinical isolates of Candida spp., in planktonic and biofilm growth stage were assessed. Additionally, the affinity of this new compound to microbial plasma membrane and hemoglobin release from human red blood cells were determined using fluorometric arid colorimetric assay, respectively. Our studies revealed that the lactone exhibits strong antifungal activity, and the ability to prevent pathogens' biofilm formation. Additionally, upon lactone treatment a significant affinity to fungal, but not to human cell membranes, indicating suitable biocompatibility was observed. (C) 2016 Elsevier Inc. All rights reserved.