[(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15R,17R,19S)-17-acetyloxy-5',7,9,13-tetramethylspiro[5,16-dioxahexacyclo[10.9.0.02,9.04,8.013,19.015,17]henicosane-6,2'-oxane]-10-yl] acetate | 160381-53-3

• 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: [(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15R,17R,19S)-17-acetyloxy-5',7,9,13-tetramethylspiro[5,16-dioxahexacyclo[10.9.0.02,9.04,8.013,19.015,17]henicosane-6,2'-oxane]-10-yl] acetate
• CAS: 160381-53-3
• 化学式: C₃₁H₄₆O₇
• 分子量: 530.702
• InChiKey: BYIAHBZIUCCORM-UVQYKJIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15R,17R,19S)-17-acetyloxy-5',7,9,13-tetramethylspiro[5,16-dioxahexacyclo[10.9.0.02,9.04,8.013,19.015,17]henicosane-6,2'-oxane]-10-yl] acetate 以 吡啶 、 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到[(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15S,18S)-15-acetyloxy-5',7,9,13-tetramethyl-16-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-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
• 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 甲基环氧丙烷 、 高氯酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 9.0h， 生成 [(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13S,15R,17R,19S)-17-acetyloxy-5',7,9,13-tetramethylspiro[5,16-dioxahexacyclo[10.9.0.02,9.04,8.013,19.015,17]henicosane-6,2'-oxane]-10-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