6β-hydroxy-5α-cholestan-3-one | 1251-95-2

• 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: 6β-hydroxy-5α-cholestan-3-one
• 英文别名: 6β-hydroxy-5α-cholestane-3-one；6β-Hydroxy-5α-cholestan-3-on；(5S,6R,8S,9S,10R,13R,14S,17R)-6-hydroxy-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: 1251-95-2
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: OVKUMALGEJVNRI-VHTRLTIZSA-N

物化性质

• 熔点：
  181-184 °C
• 沸点：
  501.3±33.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 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：

  6β-hydroxy-5α-cholestan-3-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以90%的产率得到(5alpha)-胆甾烷-3,6-二酮
  参考文献：
  名称：

  Simple NMR Determination of 5α/5β Configuration of 3-Oxosteroids

  摘要：

  提出了一种简单的方法，基于低频1H NMR光谱来区分3-氧甾体的5α-和5β-异构体。通过比较完全分配的5α-和5β-异构体的光谱，得出了额外的1H和13C NMR特征。评估了在类固醇骨架不同位置进行取代对一系列为此目的准备的异构体3-氧甾体的影响。

  DOI：

  10.1135/cccc20011529
• 作为产物：
  描述：

  5α-cholestane-3β,6β-diol 在 氢氧化钾 、 jones reagent 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 57.92h， 生成 6β-hydroxy-5α-cholestan-3-one
  参考文献：
  名称：

  Synthesis of 5.ALPHA.-cholestan-6-one derivatives with some substituents at the C-1, C-2, or C-3 position.

  摘要：

  为了研究拜耳-维利格氧化的区域选择性，我们从胆固醇合成了30种具有不同取代基（甲基、氢、乙酰氧甲基、甲氧基、乙酰氧基、苯甲酰氧基、三氟乙酰氧基、对甲苯磺酰氧基）在C-1、C-2或C-3位置的5α-胆甾烷-6-酮衍生物。通过氢硼化反应引入5α-胆甾烷-6-酮衍生物的6-氧功能团。通过使用胆固醇天然的3β-羟基，可以轻松得到3β-衍生物。通过在回流2-丁酮中使用四正丁基铵醋酸盐，将3β-甲苯磺酸酯24的构型反转得到3α-异构体。2β-异构体来自2-烯43通过溴氢化、LiAlH4还原和酯化反应得到。2β-到2α-羟基的反转通过2-氧甾体51的伯奇还原实现。1α-衍生物来自已知的6β-乙酰氧基-1α-羟基-5α-胆甾-2-烯（57）。

  DOI：

  10.1248/cpb.35.986

文献信息

• Influence of the 6-trimethylsilyl group on the fragmentation of the trimethylsilyl derivatives of some 6-hydroxy- and 3,6-dihydroxy-steroids and related compounds
  作者：David J. Harvey、Paul Vouros

  DOI：10.1002/bms.1200060402

  日期：1979.4

  The 25 eV mass spectra of the trimethylsilyl derivatives of a number of 6-hydroxy and 3,6-dihydroxy steroids together with deuterium and 18O-labeled analogs have been examined to determine the influence of the 6-OTMS group on fragmentation patterns. Ions in the cholestane series at m/z 321 and 403 were the most characteristic ions derived from the 6-OTMS function; their relative abundances, although

  已经研究了许多6-羟基和3,6-二羟基甾族化合物的三甲基甲硅烷基衍生物与氘和18O标记的类似物的25 eV质谱，以确定6-OTMS基团对断裂模式的影响。胆甾烷系列中m / z 321和403处的离子是源自6-OTMS功能的最具特征性的离子。它们的相对丰度，尽管6-OTMS类固醇本身的光谱较低，但是当存在3-OTMS或3-氧代基团时，它们的相对丰度大大提高。在雄烷和孕烷衍生物的光谱中也存在类似的离子。这些离子的丰度与C3，C5或C6的立体化学之间没有相关性。讨论了碎裂机理和气相色谱数据。
• Synthesis of ecdysone.II.Synthesis of and Stereochemistry of 2β, 3β-Dihydroxycholestan-6-ones and Their Derivatives
  作者：Hiromu Mori、Kiyoshi Tsuneda、Kenyu Shibata、Masanobu Sawai

  DOI：10.1248/cpb.15.466

  日期：——

  2β, 3β-Dihydroxycholestan-6-ones and their derivatives were prepared and their stereo chemistry was studied. In 2β, 3β-dihydroxy-or 2β, 3β-diacetoxycholestan-6-ones, equilibrium mixture consisted of 5α-and 5β-compound at the ratioof 3 : 2. On the other hand, 5α-compound was found to be exclusively stable in 2β, 3β-dihydroxycholestan-6-one acetonides.

  制备了2β,3β-二羟基胆甾坦-6-酮及其衍生物并研究了它们的立体化学。在 2β, 3β-二羟基-或 2β, 3β-二乙酰氧基胆甾烷-6-酮中，平衡混合物由 5α-和 5β-化合物以 3:2 的比例组成。另一方面，发现 5α-化合物在2β，3β-二羟基胆甾烷-6-酮丙酮化合物。
• 330. Steroids. Part II. The preparation of epicholesteryl chloride and bromide
  作者：C. W. Shoppee、G. H. R. Summers

  DOI：10.1039/jr9520001790

  日期：——
• Interactions between GABAergic and aminoacidergic pathways in the control of gonadotropin and GH secretion in pre-pubertal female rats
  作者：L. Pinilla、L. C. González、M. Tena-Sempere、Enrique Aguilar

  DOI：10.1007/bf03343970

  日期：2002.2

  Present experiments were carried out in 23-day-old female rats to analyze the interaction between excitatory amino acids (EAAs) and gamma-aminobutyric acid (GABA) in the control of gonadotropin and GH secretion. For this purpose, serum concentrations of LH, FSH and GH were measured after injection of different agonists of EAA receptor subtypes [N-methyl-D-aspartate (NMDA); kainic acid (KA), +/--alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA)], antagonists of GABA receptors (bicuculline, phaclofen) or the combined administration of both types of drugs. The results obtained indicated that: 1) GABA has a minor physiological role in the control of LH and GH secretion, since neither LH nor GH serum concentrations changed after administration of bicuculline (antagonist of GABA(A) receptors) or phaclofen (antagonist of GABA(B) receptors); 2) GABA has a sex-specific physiological role in the control of FSH secretion in female rats, in which FSH secretion increases after phaclofen administration; 3) GH secretion was enhanced after administration of NMDA, KA and AMPA, while LH increased only after activation of NMDA receptors; 4) the stimulatory effect of NMDA on LH secretion was counteracted by administration of phaclofen; and 5) bicuculline and phaclofen reduced the ability of NMDA and AMPA to stimulate GH secretion. In conclusion, present experiments evidenced a physiological role of GABA, mediated by GABA(B) receptors, in the control of FSH secretion and a cross-talk between excitatory and inhibitory amino acids in the control of anterior pituitary secretion. (C) 2002, Editrice Kurtis.
• Sterols. LXXXIV. Progesterone from Hyodesoxycholic Acid
  作者：Russell E. Marker、John Krueger

  DOI：10.1021/ja01858a019

  日期：1940.1