19-norcholesta-5,7,9-trien-3β-ol acetate | 1253-99-2

• 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: 19-norcholesta-5,7,9-trien-3β-ol acetate
• 英文别名: 3β-Acetoxy-19-nor-cholestatrien-5,7,9；[(3S,13R,14R,17R)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1253-99-2
• 化学式: C₂₈H₄₂O₂
• 分子量: 410.64
• InChiKey: VGVRNNGWKPCEFT-AZRGPZMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  19-norcholesta-5(10),6-dien-3β-ol acetate 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 19-norcholesta-5,7,9-trien-3β-ol acetate
  参考文献：
  名称：

  Synthesis of C19-functionalized 7-dehydrocholesteryl derivatives. Photochemical transformation to vitamin D3 analog

  摘要：

  DOI：

  10.1021/jo00318a024

文献信息

• Addition to steroid polyenes—I
  作者：A. van der Gen、J. Lakeman、M.A.M.P. Gras、H.O. Huisman

  DOI：10.1016/s0040-4020(01)90831-2

  日期：1964.1

  nucleophilic addition at C7 coupled with hydrogen abstraction at C9. Pyrolysis of the adduct obtained from 7-dehydrocholesterylacetate and diethyl diazodicarboxylate gives rise to the formation of 1,2-dicarbaethyoxyhydrazine and a mixture of acetoxycholestatrienes. Acid hydrolysis of the same adduct results in formation of 1,2-dicarbaethoxyhydrazine and a mixture of anthrasteroids. Structural evidence for these

  重氮二羧酸的酯显示通过在C 7的亲核加成和在C 9的夺氢与甾类5,7-二烯反应。由7-脱氢胆甾醇乙酸酯和重氮二甲酸二乙酯得到的加合物的热解导致形成1，2-二氨基甲酰氧基肼和乙酰氧基胆甾烷的混合物。相同加合物的酸水解导致形成1,2-二氨基甲乙氧基肼和蒽类固醇的混合物。这些化合物的结构证据已通过NMR光谱学获得。提出了蒽类固醇重排的一般机制。
• [EN] PRACTICAL SCREENING METHOD FOR DETECTING GENETIC DISORDERS OF STEROL METABOLISM<br/>[FR] PROCEDE DE DEPISTAGE PRATIQUE POUR LA DETECTION DES TROUBLES GENETIQUES DU METABOLISME DES STEROLS
  申请人：RICE UNIVERSITY

  公开号：WO2001092893A1

  公开（公告）日：2001-12-06

  An assay is described to screen for genetic disorders of sterol metabolism based on differences in a visual and qualitative colorimetric response and a quantitative spectrophotometric response to the Liebermann-Burchard reagent. The invention describes a qualitative and quantitative colorimetric screen for Smith-Lemli-Opitz syndrome (SLOS). The invention also relates to diagnosis of SLOS by nuclear magnetic resonance of a sample containing sterols, which can distinguish mild cases of SLOS from normal subjects by determination of individual noncholesterol sterols. Further, the invention describes the treatment of Guthrie cards to delay, slow, or prevent decomposition of sterols during storage.