2α-azido-5α-cholestan-3-one | 35647-02-0

• 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-5α-cholestan-3-one
• 英文别名: 2α-azidocholestan-3-one；2-Azidocholestan-3-one；2α-Azidocholestan-3-on；(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-one
• CAS: 35647-02-0
• 化学式: C₂₇H₄₅N₃O
• 分子量: 427.674
• InChiKey: XXMNHGDDXBYXQL-RRFIWRICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  31
• 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：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2α-azido-5α-cholestan-3-one 在 吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 99.5h， 生成 (17β-Acetoxyandrostano<2,3-b>)cholestano<2,3-e>pyrazine
  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：

  2α-bromo-5α-cholestan-3-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以89%的产率得到2α-azido-5α-cholestan-3-one
  参考文献：
  名称：

  An efficient method for the synthesis of methyl 11α-amino-3α,7α-diacetoxy-12-oxo-5β-cholan-24-oate

  摘要：

  The synthesis of methyl 11 alpha-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate, methyl 11 beta-azido-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate and methyl 11 alpha-amino-3 alpha,7 alpha-diacetoxy-12-oxo-5 beta-cholan-24-oate have been achieved. Mechanistic aspects for the decomposition of steroidal azidoketones to its enamines are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.073

文献信息

• Synthesis of N , N -bis[2-(2-pyridyl)ethyl]amino steroids and related compounds intended as chiral ligands for copper ions
  作者：Manuela Gonschior、Manuela Kötteritzsch、Matthias Rost、Bruno Schönecker、Ralf Wyrwa

  DOI：10.1016/s0957-4166(00)00168-3

  日期：2000.6

  N-bis[2-(2-pyridyl)ethyl]amino structure (RPY2) are useful tridentate ligands for copper(I) ions, which can bind and activate oxygen from the atmosphere. For diastereoselective and enantioselective oxidation reactions, hitherto unknown chiral ligands possessing tripodal structures have been synthesized starting from homochiral steroids. The double Michael addition of primary steroidal amines and aminoalcohols

  具有N，N-双[2-（2-吡啶基）乙基]氨基结构（RPY2）的化合物对于铜（I）离子是有用的三齿配体，它可以结合并激活大气中的氧气。对于非对映选择性和对映选择性氧化反应，迄今未知的具有三脚架结构的手性配体是从同手性类固醇开始合成的。伯类固醇胺和氨基醇向2-乙烯基吡啶的双迈克尔加成反应不是很成功。然而，在大多数情况下，可以通过该方法获得具有N- [2-（2-吡啶基）乙基]氨基甾类结构的同手性双齿配体。新路线（用2-吡啶基乙酸接着BH 3酰化二齿配体）·描述了在空间位阻位置也将THF还原或类固醇酮的还原胺化，酰化和硼烷还原）成所需的三齿RPY2。在最后的反应顺序中，也可以得到“混合的”三齿配体。简要讨论了铜与这些配体的络合和氧活化作用。
• A convenient procedure for the synthesis of bis-steroidal pyrazines: models for the cephalostatins
  作者：Stephen C. Smith、Clayton H. Heathcock

  DOI：10.1021/jo00050a002

  日期：1992.11

  Efficient routes have been developed for both symmetrical and unsymmetrical bis-steroidal pyrazines from readily available precursors.
• Takahashi, Thomas T.; Satoh, James Y., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1916 - 1919
  作者：Takahashi, Thomas T.、Satoh, James Y.

  DOI：——

  日期：——
• Takahashi, Thomas T.; Satoh, James Y.; Saitoh, Kouichi, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2277 - 2280
  作者：Takahashi, Thomas T.、Satoh, James Y.、Saitoh, Kouichi

  DOI：——

  日期：——
• 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：——