2α-Azido-3-(hydroxyimino)cholestane | 89684-81-1

• 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: 2α-Azido-3-(hydroxyimino)cholestane
• 英文别名: 2α-azido-5α-cholestan-3-one oxime；2α-azido-5α-cholestan-3-one (E)-oxime；(NE)-N-[(2R,5S,8R,9S,10S,13R,14S,17R)-2-azido-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine
• CAS: 89684-81-1
• 化学式: C₂₇H₄₆N₄O
• 分子量: 442.688
• InChiKey: OVEYKEXGDOZNSJ-LKLUYDFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2α-Azido-3-(hydroxyimino)cholestane 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 0.33h， 以94%的产率得到[(3R,3aR,5aS,6S,7S,9aR,9bS)-7-Cyanomethyl-3-((R)-1,5-dimethyl-hexyl)-3a,6-dimethyl-dodecahydro-cyclopenta[a]naphthalen-6-yl]-acetonitrile
  参考文献：
  名称：

  α-叠氮-甾体酮肟的CC键断裂

  摘要：

  在标准贝克曼条件下，将α-叠氮-甾族肟裂解以提供单氰基和二氰基衍生物。

  DOI：

  10.1039/c39830001441
• 作为产物：
  描述：

  2α-azido-5α-cholestan-3-one 在 吡啶 、 盐酸羟胺 作用下， 反应 0.5h， 生成 2α-Azido-3-(hydroxyimino)cholestane
  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

文献信息

• C–C bond-cleavage of α-azido-steroidal ketoximes
  作者：Thomas T. Takahashi、K. Nomura、James Y. Satoh

  DOI：10.1039/c39830001441

  日期：——

  α-Azido-steroidal oximes were cleaved to provide mono- and di-cyano derivatives under standard Beckmann conditions.

  在标准贝克曼条件下，将α-叠氮-甾族肟裂解以提供单氰基和二氰基衍生物。
• Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1
  作者：Clayton H. Heathcock、Stephen C. Smith

  DOI：10.1021/jo00101a052

  日期：1994.11

  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.
• Takahashi, Thomas T.; Satoh, James Y.; Nomura, K., Journal of the Chemical Society. Perkin transactions I, 1986, p. 909 - 912
  作者：Takahashi, Thomas T.、Satoh, James Y.、Nomura, K.

  DOI：——

  日期：——