3β-hydroxycholest-5-en-23-one | 27241-01-6

• 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: 3β-hydroxycholest-5-en-23-one
• 英文别名: 23-ketocholesterol；3β-hydroxy-cholest-5-en-23-one；3β-Hydroxy-cholest-5-en-23-on；3β-Hydroxycholest-5-en-23-on；(2R)-2-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-4-one
• CAS: 27241-01-6
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: SQXINCAREXIEIA-ROOYLRQDSA-N

物化性质

• 沸点：
  508.5±23.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-hydroxycholest-5-en-23-one 以97%的产率得到胆固醇
  参考文献：
  名称：

  Stereocontrolled synthesis of sterol side chains

  摘要：

  DOI：

  10.1021/ja00522a080
• 作为产物：
  描述：

  3β-acetoxy-24-nor-chol-5-en-23-oic acid 在 氯化亚砜 、 乙醚 、 苯 作用下， 生成 3β-hydroxycholest-5-en-23-one
  参考文献：
  名称：

  Bending strength and toughness of heat-treated wood

  摘要：

  The load-deflection curve for static bending and the force-time curve for impact bending of heat-treated wood were examined in detail. The effect of oxygen in air was also investigated. Sitka spruce (Picea sitchensis Carr.) was heated for 0.5-16.0h at a temperature of 160 degrees C in nitrogen gas or air. The dynamic Young's modulus was measured by the free-free flexural vibration test, the static Young's modulus and work needed for rupture by the static bending test, and the absorbed energy in impact bending by the impact bending test. The results obtained were as follows: (1) The static Young's modulus increased at the initial stage of the heat treatment and decreased later. It decreased more in air than in nitrogen. (2) The bending strength increased at the initial stage of the heat treatment and decreased later. It decreased more in air than in nitrogen. (3) The work needed for rupture decreased steadily as the heating lime increased. It decreased more in nitrogen than in air. It is thought that heat-treated wood was more brittle than untreated wood in the static bending test because , was reduced by the heat treatment. This means that the main factors contributing to the reduction of the work needed for rupture were viscosity and plasticity, not elasticity. (4) The absorbed energy in impact bending increased at the initial stage of the heat treatment and decreased later. It decreased more in air than in nitrogen. It was concluded that heat-treated wood became more brittle in the impact bending test because I-12 and I-23, were reduced by the heat treatment.

  DOI：

  10.1007/bf00779547

文献信息

• Meiosis regulating compounds
  申请人：——

  公开号：US20030032824A1

  公开（公告）日：2003-02-13

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物与天然化合物结构相关，可以从公牛睾丸和人类卵泡液中提取，用于调节卵母细胞和雄性生殖细胞的减数分裂。其中一些化合物在不孕症治疗中很有用，而其他化合物则可用作避孕药。这些化合物具有结构式1，其中取代基如规范中所定义。
• Process for producing steroid compounds having an oxogroup in the side chain
  申请人：TEIJIN LIMITED

  公开号：EP0013082A1

  公开（公告）日：1980-07-09

  A process for producing a steroid compound having an oxo group in the side chain, which comprises condensing an acid halide having a steroid skeleton with an organozinc compound at a halocarbonyl group of the acid halide in an inert organic medium in the presence of a catalytic amound of an ether capable of forming a complex with the organozinc compound and, if desired, hydrolyzing the product. The process gives the steroid compound in a high yield, and often in an almost quantitative yield. The steroid compound can be an important intermediate for the production of vitamin D3 analogs, such as active forms of vitamin D3.

  一种生产侧链中含有氧代基团的甾体化合物的工艺，包括在惰性有机介质中，在能与有机锌化合物形成络合物的醚的催化下，在酸卤化物的卤代羰基上将具有甾体骨架的酸卤化物与有机锌化合物缩合，并在需要时水解产物。该工艺可以得到高产率的甾体化合物，通常几乎可以达到定量产率。类固醇化合物可以作为生产维生素 D3 类似物（如活性维生素 D3）的重要中间体。
• First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols
  作者：Michael E Jung、Ted W Johnson

  DOI：10.1016/s0040-4020(00)01086-3

  日期：2001.2

  The novel pentacyclic polyhydroxylated sterol, xestobergsterol A la, a strong inhibitor of histamine release from rat mast cells induced by anti-IgE, has been synthesized in 24 steps and good overall yield From stigmasterol 7. The Breslow remote functionalization process has been extended to several more highly functionalized steroid derivatives, especially those with oxygen functionality in the B-ring. The key steps of the synthesis of xestobergsterol A la and its analogues, 7-deoxyxestobergsterol A Id and 16,23-seco-23-deoxyxestobergsterol A 73, are the Breslow remote functionalization of oxygenated steroids and for compounds la and Id, a novel base-catalyzed epimerization-aldol condensation of a dione to give the desired CD-cis ring structure of the xestobergsterols. Thus the known alcohol 75, prepared from stigmasterol 7, was taken to the tetraacetate 107 which was then converted via a Breslow remote functionalization into the alkene aldehyde 114 which was transformed in 5 steps to xestobergsterol A la. Testing of the synthetic materials showed that the two analogues, 7-deoxyxestobergsterol A Ib and 16,23-seco-23-deoxyxestobergsterol A 73, are also potent inhibitors of histamine release with ICS, values (IC50 500 nM and 750 nM, respectively) being only 1015 times less than that of xestobergsterol A itself (50 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of 23-ketocholestane derivatives with different side-chain lengths (asterosapogenin analogs)
  作者：I. A. Kutnevich、I. G. Reshetova、E. I. Chernoburova、A. V. Kamernitskii

  DOI：10.1007/bf00958594

  日期：1991.4

  Syntheses were developed for 23-ketoasterosapogenin analogs with various side-chain lengths from dimethyl(tert-butyl)silyloxypregnenolone (DMTBS-pregnenolone) through 20-hydroxy-23-carboxylates or 22-acetylenic (C5, C6) derivatives by reduction and allylic rearrangement with concurrent oxidation of the intermediate 23-hydroxy-27-nor- and 27-nor-26-methylcholestanes.
• Sterol Metabolism X: Epimeric 23-Hydroxycholesterols
  作者：Johan E. Van Lier、Leland L. Smith

  DOI：10.1002/jps.2600590535

  日期：1970.5