3α-acetoxy-16-hydroxy-5β-bisnorcholanic acid-(22->16) lactone | 866784-52-3

• 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: 3α-acetoxy-16-hydroxy-5β-bisnorcholanic acid-(22->16) lactone
• 英文别名: 3α-acetoxy-16β-hydroxy-5β-bisnorcholanic acid (22->16) lactone；3α-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone；3α-acetoxy-16β-hydroxy-23,24-dinor-5β-cholan-22-oic acid-lactone；3α-Acetoxy-16β-hydroxy-23,24-dinor-5β-cholan-22-saeure-lacton；[(1R,2S,4S,7S,8R,9S,12S,13S,16R,18R)-7,9,13-trimethyl-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] acetate
• CAS: 866784-52-3
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: HUESGZPZXJYYMK-DZUATTBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (25R)-3α-acetoxy-5β-spirostan-23-one 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以98.3%的产率得到3α-acetoxy-16-hydroxy-5β-bisnorcholanic acid-(22->16) lactone
  参考文献：
  名称：

  Studies on the BF3·Et2O catalyzed Baeyer–Villiger reaction of spiroketalic steroidal ketones

  摘要：

  During reactions of 23-oxosapogenins and the corresponding isomeric 22-oxo-23-spiroketals with MCPBA in the presence of BF3 center dot Et2O, equilibration occurs between the ketones. The Baeyer-Villiger type oxidation is followed by fragmentation to the dinorcholanic lactones and 3-methylbutyrolactone. The mechanistic aspects of these reactions in the 25R and 25S series are discussed. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.12.004

文献信息

• Mechanistic insights and new products of the reaction of steroid sapogenins with NaNO2 and BF3·Et2O in acetic acid
  作者：Yliana López、Karen M. Ruíz-Pérez、Rebeca Yépez、Rosa Santillan、Marcos Flores-Alamo、Martín A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2008.02.003

  日期：2008.7

  A detailed analysis of the course of the reaction of steroid sapogenins with NaNO(2) and BF(3).Et(2)O in acetic acid is presented and some evidences on the involved mechanism are provided. Two new products of the studied reaction were isolated and unambiguously characterized with the aid of NMR and single crystal X-ray diffraction.

  详细分析了类固醇皂甙元与NaNO（2）和BF（3）.Et（2）O在乙酸中的反应过程，并提供了有关其参与机理的一些证据。分离了所研究反应的两种新产物，并借助NMR和单晶X射线衍射对其进行了明确的表征。
• The unexpected course of the reaction of steroid sapogenins with diacetoxyiodobenzene and BF3·Et2O in formic acid
  作者：Martín A. Iglesias-Arteaga、Rafael O. Arcos-Ramos、José M. Méndez-Stivalet

  DOI：10.1016/j.tetlet.2007.08.071

  日期：2007.10

  The reaction of steroid sapogenins of both the 25R and 25S series with diacetoxyiodobenzene and BF3·Et2O in formic acid produced a mixture of an equatorial 23-formyloxysapogenin, a 16β,23:23,26-diepoxy-22-one and a bisnorcholanic lactone. The outcome of this reaction, that drastically differs from the same reaction in acetic acid, opens up new possibilities for the transformation of the side chain

  25 R和25 S系列甾体皂甙元与二乙酰氧基碘苯和BF 3 ·Et 2 O在甲酸中的反应产生了赤道23-甲酰氧基皂甙元的混合物，即16β，23：23,26-双环氧-22-和双降胆固醇内酯。该反应的结果与乙酸中的同一反应完全不同，为类固醇皂苷元侧链的转化开辟了新的可能性。
• Beckmann reactions of steroidal spirocyclic oximes derived from the 16β,23:23,26-diepoxy-22-oxo moiety
  作者：Mariana Macías-Alonso、Marcos Flores-Alamo、Martín A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2008.09.013

  日期：2009.1

  The Beckmann rearrangement of the syn and anti isomers of the spirocyclic oxime derived from a 16beta,23:23,26-diepoxy-5beta-cholestan-22-one was studied. Whereas the anti isomer always follows the Beckmann fragmentation course, the syn isomer, depending on the reaction conditions, follows the normal Beckmann rearrangement course and/or the isomerization to the anti isomer followed by the fragmentation

  对衍生自 16beta,23:23,26-diepoxy-5beta-cholestan-22-one 的螺环肟的顺式和反异构体的贝克曼重排进行了研究。反异构体总是遵循贝克曼断裂过程，而顺式异构体根据反应条件遵循正常的贝克曼重排过程和/或异构化为反异构体，然后是断裂过程。
• Sterols. LXXXIII. Oxidation Products of Sarsasapogenin. Studies on the C₂₂ Lactone
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01858a018

  日期：1940.1
• Steroids. Part XII. The structures of cholegenin and isocholegenin
  作者：Y. Mazur、F. S. Spring

  DOI：10.1039/jr9540001223

  日期：——