[(5S,5'R,6S,9R,10R,13S,14R,17S,23S,24S,26R,27S,28R,29S,30R,32S,34S,35R,38S)-5,5',9,23,27,29-hexamethyl-10-[(2R)-6-methylheptan-2-yl]spiro[31-oxa-2,20-diazadecacyclo[19.18.0.03,19.05,17.06,14.09,13.023,38.024,35.027,34.028,32]nonatriaconta-1,3(19),20-triene-30,2'-oxane]-26-yl] acetate | 160381-59-9

• 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: [(5S,5'R,6S,9R,10R,13S,14R,17S,23S,24S,26R,27S,28R,29S,30R,32S,34S,35R,38S)-5,5',9,23,27,29-hexamethyl-10-[(2R)-6-methylheptan-2-yl]spiro[31-oxa-2,20-diazadecacyclo[19.18.0.03,19.05,17.06,14.09,13.023,38.024,35.027,34.028,32]nonatriaconta-1,3(19),20-triene-30,2'-oxane]-26-yl] acetate
• CAS: 160381-59-9
• 化学式: C₅₆H₈₆N₂O₄
• 分子量: 851.31
• InChiKey: ZDDWUUPJCDBABV-ZPRRQKDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  62
• 可旋转键数：
  7
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(5S,5'R,6S,9R,10R,13S,14R,17S,23S,24S,26R,27S,28R,29S,30R,32S,34S,35R,38S)-5,5',9,23,27,29-hexamethyl-10-[(2R)-6-methylheptan-2-yl]spiro[31-oxa-2,20-diazadecacyclo[19.18.0.03,19.05,17.06,14.09,13.023,38.024,35.027,34.028,32]nonatriaconta-1,3(19),20-triene-30,2'-oxane]-26-yl] acetate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以85%的产率得到(5S,5'R,6S,9R,10R,13S,14R,17S,23S,24S,26R,27S,28R,29S,30R,32S,34S,35R,38S)-5,5',9,23,27,29-hexamethyl-10-[(2R)-6-methylheptan-2-yl]spiro[31-oxa-2,20-diazadecacyclo[19.18.0.03,19.05,17.06,14.09,13.023,38.024,35.027,34.028,32]nonatriaconta-1,3(19),20-triene-30,2'-oxane]-26-ol
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052
• 作为产物：
  描述：

  (1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,18S)-10-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-one 在 4-二甲氨基吡啶 、 oxodiperoxomolybdenum-pyridine-dimethylpyrrolidinone 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 54.83h， 生成 [(5S,5'R,6S,9R,10R,13S,14R,17S,23S,24S,26R,27S,28R,29S,30R,32S,34S,35R,38S)-5,5',9,23,27,29-hexamethyl-10-[(2R)-6-methylheptan-2-yl]spiro[31-oxa-2,20-diazadecacyclo[19.18.0.03,19.05,17.06,14.09,13.023,38.024,35.027,34.028,32]nonatriaconta-1,3(19),20-triene-30,2'-oxane]-26-yl] acetate
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052