烯胆固烷酮 | 15459-85-5

• 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
• 中文名称: 烯胆固烷酮
• 英文名称: 5α-cholest-7-en-3-one
• 英文别名: 5α-Cholest-7-en-3-on；5α-Cholesten-(7)-on-(3)；lathosterone；Cholest-7-en-3-on；5alpha-Cholest-7-en-3-one；(5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 15459-85-5
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: FLRPNSKUGCVRRB-IINKENNYSA-N

物化性质

• 保留指数：
  3150

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  烯胆固烷酮 在 Lindlar's catalyst 喹啉 、 碳酸氢锂 、 氢气 、 phenyltrimethylammonium tribromide 、 lithium chloride 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 胆甾-4,7-二烯-3-酮
  参考文献：
  名称：

  Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis in Locusta migratoria

  摘要：

  We have synthesized a tritiated form of 14-alpha-hydroxy-5-beta-cholest-7-ene-3,6-dione (5-beta-diketol) of high specific activity (1.74 TBq/mmol) from 7-dehydrocholesterol in seven steps with stereoselective introduction of the A/B cis ring junction as the key reaction. We have examined the ability of endocrine glands (prothoracic glands) of Locusta migratoria to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. A very efficient conversion of 5-beta-diketol to ecdysone and to 3-dehydroecdysone was monitored, which opens up new possibilities for the understanding of the role of 3-dehydro-compounds in ecdysteroid biosynthesis.

  DOI：

  10.1016/s0040-4020(01)96161-7
• 作为产物：
  描述：

  cholesterol 在 吡啶 、 丙醇 、 乙醇 、 sodium 、 aluminium(III) phenoxide 、 丙酮 、 苯 作用下， 生成 烯胆固烷酮
  参考文献：
  名称：

  ?-Cholestenon und epi-?-Cholestenon

  摘要：

  DOI：

  10.1002/hlca.19470300532

文献信息

• LIGANDS FOR NEMATODE NUCLEAR RECEPTORS AND USES THEREOF
  申请人：Mangelsdorf J. David

  公开号：US20070219173A1

  公开（公告）日：2007-09-20

  Anti-nematode compounds, compositions, and methods for identifying such compounds are disclosed, where the compounds have the formula I: where Q, Q′, R 1 , R 2 , and n are defined herein.

  本文披露了抗线虫化合物、组合物以及鉴定这种化合物的方法，其中化合物的公式为I：其中Q、Q'、R1、R2和n的定义如本文所述。
• A Novel 3-Hydroxysteroid Dehydrogenase That Regulates Reproductive Development and Longevity
  作者：Joshua Wollam、Daniel B. Magner、Lilia Magomedova、Elisabeth Rass、Yidong Shen、Veerle Rottiers、Bianca Habermann、Carolyn L. Cummins、Adam Antebi

  DOI：10.1371/journal.pbio.1001305

  日期：——

  A multidisciplinary approach identifies novel biochemical activities involved in the synthesisof C. elegans bile acid-like steroids, which act as hormones that regulate sterol metabolism and longevity.

  一种多学科方法发现了参与合成大花蛛胆汁酸类固醇的新型生化活动，胆汁酸类固醇是调节固醇代谢和寿命的激素。
• Cholesterol and Companions. II. Exhaustive Dichromate Oxidation
  作者：Louis F. Fieser

  DOI：10.1021/ja01114a002

  日期：1953.9
• Barnes,M.H.; Whalley,W.B., Journal of the Chemical Society. Perkin transactions I, 1977, p. 828 - 832
  作者：Barnes,M.H.、Whalley,W.B.

  DOI：——

  日期：——
• Novel nuclear methylation of sterols by the nematode caenorhabditis elegans
  作者：David J. Chitwood、William R. Lusby、Ruben Lozano、Malcolm J. Thompson、James A. Svoboda

  DOI：10.1016/0039-128x(83)90042-9

  日期：1983.9

  Caenorhabditis elegans possesses a unique sterol methylation pathway not reported to occur in any other organism and also removes the C-24 ethyl group of sitosterol (a plant sterol). This nematode produced substantial quantities of 4 alpha-methyl-5 alpha-cholest-8(14)-en-3 beta-ol and smaller amounts of lophenol from dietary cholesterol, desmosterol or sitosterol. When C. elegans was propagated in media containing sitosterol plus 25-azacoprostane hydrochloride (25-aza-5 beta-cholestane hydrochloride), an inhibitor of delta 24-sterol reductase in insects, its 4 alpha-methylsterol fraction largely consisted of equal amounts of 4 alpha-methyl-5 alpha-cholesta-7,24-dien-3 beta-ol and 4 alpha-methyl-5 alpha-cholesta-8(14),24-dien-3 beta-ol. Thus 25-azacoprostane hydrochloride inhibited both a delta 24-sterol reductase and a delta 7-sterol isomerase in C. elegans.