(E)-3-Phenyl-acrylic acid (8R,9R,10S,11S,13S,14S)-12-acetoxy-3,14-dihydroxy-17-(1-hydroxy-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-yl ester | 13872-76-9

• 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: (E)-3-Phenyl-acrylic acid (8R,9R,10S,11S,13S,14S)-12-acetoxy-3,14-dihydroxy-17-(1-hydroxy-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-yl ester
• 英文别名: condurangogenin C
• CAS: 13872-76-9
• 化学式: C₃₂H₄₄O₇
• 分子量: 540.697
• InChiKey: FKXVPEBFIHNLPS-PDSYNOBHSA-N

物化性质

• 沸点：
  654.4±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  113.29
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (E)-3-Phenyl-acrylic acid (8R,9R,10S,11S,13S,14S)-12-acetoxy-3,14-dihydroxy-17-(1-hydroxy-ethyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-yl ester 以 吡啶 为溶剂， 反应 24.0h， 以495 mg的产率得到condurangogenin C 3-acetate
  参考文献：
  名称：

  Studies on the constituents of asclepiadaceae plants. XLIX. Confirmation of the structures of antitumor-active glycosides in condurango cortex. Chemical transformation of the aglycone moiety.

  摘要：

  In order to confirm the structure of condurangogenin B, which is the aglycone of antitumor-active condurango glycoside (CG) B0, the hypoiodite reaction of condurangogenin C 3-acetate, was carried out. A mixture of condurangogenin C 3-acetate, Pb (OAc)4, I2, CaCO3, and diethyl ether was irradiated under nitrogen using a tungsten lamp. HPLC separation of the reaction products gave three compounds, P-1, P-2, and P-3. The structures of these compounds were determined from the spectroscopic data. The PMR and mass spectra of P-1 were essentially identical with those of condurangogenin B 3-acetate. Thus, the ester linkage positions (11-cinnamoyl, 12-acetyl) and the ketal structure of conduragogenin B were confirmed. As CGD0, 20-O-methyl-CGD0, and 20-iso-O-methyl-CGD0 could be converted chemically to CGB0, these glycosides have the same positions of ester linkages as CGB0.

  DOI：

  10.1248/cpb.30.2429

文献信息

• Studies on the constituents of asclepiadaceae plants. XLIX. Confirmation of the structures of antitumor-active glycosides in condurango cortex. Chemical transformation of the aglycone moiety.
  作者：MUNEAKI TAKASE、SUMIO TERADA、HAJIME YAMAMOTO、TOSHIHARU NARITA、MASAHIKO KIMURA、KOJI HAYASHI、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.30.2429

  日期：——

  In order to confirm the structure of condurangogenin B, which is the aglycone of antitumor-active condurango glycoside (CG) B0, the hypoiodite reaction of condurangogenin C 3-acetate, was carried out. A mixture of condurangogenin C 3-acetate, Pb (OAc)4, I2, CaCO3, and diethyl ether was irradiated under nitrogen using a tungsten lamp. HPLC separation of the reaction products gave three compounds, P-1, P-2, and P-3. The structures of these compounds were determined from the spectroscopic data. The PMR and mass spectra of P-1 were essentially identical with those of condurangogenin B 3-acetate. Thus, the ester linkage positions (11-cinnamoyl, 12-acetyl) and the ketal structure of conduragogenin B were confirmed. As CGD0, 20-O-methyl-CGD0, and 20-iso-O-methyl-CGD0 could be converted chemically to CGB0, these glycosides have the same positions of ester linkages as CGB0.