25-hydroxy-5α-cholestan-3β-yl acetate | 2550-91-6

• 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: 25-hydroxy-5α-cholestan-3β-yl acetate
• 英文别名: 3β-Acetoxy-25-hydroxy-5α-cholestane；3β-acetoxy-5α-cholestan-25-ol；5α-Cholestan-3β,25-diol-3-monoacetat；3beta-Acetoxy-25-hydroxy-5alpha-cholestane；[(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 2550-91-6
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: JKKYDIZVQGOJLZ-AMPBYXCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5α-cholestan-3β-yl acetate 在 甲基(三氟甲基)-1,3-二环氧丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到25-hydroxy-5α-cholestan-3β-yl acetate
  参考文献：
  名称：

  Oxidation of natural targets by dioxiranes. 2. Direct hydroxylation at the side chain C-25 of cholestane derivatives and of vitamin D3 Windaus-Grundmann ketone

  摘要：

  The direct, high-yield oxyfunctionalization of the side-chain C-25 of 5-alpha-cholestan-3-one, 3-beta-acetoxy-5-alpha-cholestane, and 5-alpha,6-beta-Br2-3-beta-acetoxycholestane as well as of the vitamin D3-derived Windaus-Grundmann ketone has been achieved under mild conditions employing either dimethyldioxirane or its trifluoromethyl analogue.

  DOI：

  10.1021/jo00045a004

文献信息

• Regioselective Oxyfunctionalization of Unactivated Carbons in Steroids by a Model of Cytochrome P-450:  Osmiumporphyrin Complex/<i>tert</i>-Butyl Hydroperoxide System
  作者：Takashi Iida、Shoujiro Ogawa、Keiji Hosoi、Mitsuko Makino、Yasuo Fujimoto、Takaaki Goto、Nariyasu Mano、Junichi Goto、Alan F. Hofmann

  DOI：10.1021/jo061800g

  日期：2007.2.1

  tert-Butyl hydroperoxide catalyzed by (5,10,15,20-tetramesitylporphyrinate) osmium(II) carbonyl [Os(TMP)CO] complex was found to be a highly efficient versatile oxidant for C−H carbons in steroid substrates. When reacted with representative steroids with an estrane, pregnane, 5β-cholane, or 5α-cholestane structure, regioselective oxyfunctionalization and/or oxidative degradation occurred to give a

  发现（5,10,15,20-四氢卟啉）（II）羰基[（Os（TMP）CO]络合物催化的叔丁基氢过氧化物是甾族化合物基质中CH碳的高效通用氧化剂。当与具有雌激素，孕烷，5β-胆甾醇或5α-胆甾烷结构的代表性类固醇反应时，发生区域选择性的氧官能化和/或氧化降解，从而一步生成多种新颖且不常见的衍生物。
• A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane†
  作者：Takashi Iida、Takeru Yamaguchi、Ryusei Nakamori、Masahiro Hikosaka、Nariyasu Mano、Junichi Goto、Toshio Nambara

  DOI：10.1039/b104938k

  日期：——

  Oxyfunctionalization of unactivated methine carbon atoms with dimethyldioxirane (DMDO) is studied for various substituted steroids related to the 5β-cholane and 5α-cholestane series. A highly efficient, stereoselective, one-step remote oxidation of specific methine carbons is attained by DMDO oxidation under mild conditions to give a variety of novel mono- and dihydroxylated steroids. The reactivity and site selectivity

  研究了二甲基二环氧乙烷（DMDO）对未活化次甲基碳原子的氧官能化作用 类固醇 与5β-胆烷有关 5α-胆甾烷系列。高效，立体选择的一步式遥控器氧化作用 DMDO可实现特定的次甲基碳 氧化作用 在温和的条件下产生各种新颖的单羟基和二羟基 类固醇。远程氧官能化的反应性和位点选择性受结构和空间环境以及分子中目标次甲基碳原子的电子密度程度的影响。非酶促方法可有效地应用于生物活性物质的有效和短步合成类固醇。
• Preparation of derivatives of cholesterol
  申请人：——

  公开号：US03963765A1

  公开（公告）日：1976-06-15

  Process for the production of hydroxylated derivatives of cholesterol and 7-dehydrocholesterol which comprises subjecting a saturated unsubstituted or substituted derivative of cholestane, dissolved in a suitable solvent, in the presence of peracetic acid, to irradiation with ultra-violet radiation of a wavelength below 350m.mu. , or heating in a suitable solvent, separating the reaction products, which if desired, are converted to other derivatives, and recovering the residue of the starting material. Novel derivatives are obtained and these are: 3.beta.-acetoxy,25-hydroxy,5.alpha.-cholestane; 3.beta.-acetoxy, 5.alpha.,25-dihydroxy cholestane; 3.beta.,5.alpha.,25-trihydroxy cholestane; 3-keto, 5.alpha.,25-dihydroxy cholestane; 3-keto,25-hydroxy-.DELTA..sup.4 -cholestane; 3.beta.,25-diacetoxy-5.alpha.-hydroxy-cholestane; 3.beta.-acetoxy, 25-trichloroacetoxy-5.alpha.-hydroxy-cholestane, 25-trichloroacetoxy-cholesterol and 25-acetoxy-cholesterol.

  生产胆固醇和7-去氢胆固醇的羟基衍生物的过程包括将饱和未取代或取代的胆固醇衍生物溶解在适当的溶剂中，在过氧乙酸的存在下，经过紫外线辐射波长低于350m.mu.或在适当的溶剂中加热，分离反应产物，如果需要，将其转化为其他衍生物，并恢复起始材料的残留物。得到新的衍生物，包括：3-β-乙酰氧基，25-羟基，5-α-胆固醇烷；3-β-乙酰氧基，5-α，25-二羟基胆固醇烷；3-β，5-α，25-三羟基胆固醇烷；3-酮，5-α，25-二羟基胆固醇烷；3-酮，25-羟基-Δ4-胆固醇烷；3-β，25-二乙酰氧基-5-α-羟基-胆固醇烷；3-β-乙酰氧基，25-三氯乙酰氧基-5-α-羟基-胆固醇烷，25-三氯乙酰氧基-胆固醇和25-乙酰氧基胆固醇。
• Hoffmeister,H. et al., Chemische Berichte, 1965, vol. 98, p. 2369 - 2375
  作者：Hoffmeister,H. et al.

  DOI：——

  日期：——