cholesta-5,8-dien-3-one | 259659-60-4

• 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: cholesta-5,8-dien-3-one
• 英文别名: (10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,7,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 259659-60-4
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: IIIVKPWHGBRLRN-OQHNQDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  cholesta-5,8-dien-3-one 在 吡啶 、 sodium borotritide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis of [3α-3H]cholesta-5,8-dien-3β-ol and tritium-labeled forms of other sterols of potential importance in the Smith-Lemli-Optiz syndrome⋆

  摘要：

  Five unsaturated sterols relevant to the Smith-Lemli-Opitz syndrome have been prepared in high radiochemical purity with a tritium label at the 3 alpha position. Swern oxidation of cholesta-5,8-dien-3 beta-ol and other unlabeled C-27 sterols afforded the corresponding 3-ketosteroids, and reduction with tritiated NaBH4 gave the desired 3 alpha-H-3 sterols, with double bonds at the Delta(5,8), Delta(5,8(14)), Delta(6,8), Delta(6,8(14)), and Delta(8) positions. High radiochemical purity of the tritiated sterols was demonstrated by normal phase, reversed phase, and silver-ion (Ag+) high-performance liquid chromatography (HPLC). In the course of this work, we developed a medium-pressure variant of Ag+-HPLC for purifying radiolabeled samples, documented significant isotopic fractionation of the 3 alpha-tritiated sterols and their acetates on Ag+-HPLC, and discovered unexpected effects of a Delta(8(14)) bond on the conformation of 3-keto-Delta(5)-steroids. The synthetic and analytical methodologies described herein should provide a sound basis for investigating the origin and metabolism of sterols involved in the Smith-Lemli-Opitz syndrome and in late stages of cholesterol biosynthesis. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00079-3
• 作为产物：
  描述：

  (3S,10S,13R,14R,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,11,12,14,15,16,17-十氢-1H-环戊二烯并[a]菲-3-醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到cholesta-5,8-dien-3-one
  参考文献：
  名称：

  Synthesis of [3α-3H]cholesta-5,8-dien-3β-ol and tritium-labeled forms of other sterols of potential importance in the Smith-Lemli-Optiz syndrome⋆

  摘要：

  Five unsaturated sterols relevant to the Smith-Lemli-Opitz syndrome have been prepared in high radiochemical purity with a tritium label at the 3 alpha position. Swern oxidation of cholesta-5,8-dien-3 beta-ol and other unlabeled C-27 sterols afforded the corresponding 3-ketosteroids, and reduction with tritiated NaBH4 gave the desired 3 alpha-H-3 sterols, with double bonds at the Delta(5,8), Delta(5,8(14)), Delta(6,8), Delta(6,8(14)), and Delta(8) positions. High radiochemical purity of the tritiated sterols was demonstrated by normal phase, reversed phase, and silver-ion (Ag+) high-performance liquid chromatography (HPLC). In the course of this work, we developed a medium-pressure variant of Ag+-HPLC for purifying radiolabeled samples, documented significant isotopic fractionation of the 3 alpha-tritiated sterols and their acetates on Ag+-HPLC, and discovered unexpected effects of a Delta(8(14)) bond on the conformation of 3-keto-Delta(5)-steroids. The synthetic and analytical methodologies described herein should provide a sound basis for investigating the origin and metabolism of sterols involved in the Smith-Lemli-Opitz syndrome and in late stages of cholesterol biosynthesis. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00079-3

文献信息

• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  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.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• MEIOSIS REGULATING COMPOUNDS
  申请人：NOVO NORDISK A/S

  公开号：EP0946584A1

  公开（公告）日：1999-10-06
• US6486145B2
  申请人：——

  公开号：US6486145B2

  公开（公告）日：2002-11-26
• US6759400B2
  申请人：——

  公开号：US6759400B2

  公开（公告）日：2004-07-06
• [EN] MEIOSIS REGULATING COMPOUNDS<br/>[FR] COMPOSES REGULATEURS DE MEIOSE
  申请人：NOVO NORDISK A/S

  公开号：WO1998028323A1

  公开（公告）日：1998-07-02

  (EN) Certain compounds, structurally related to natural compounds which can be extracted $i(i.a.) from bull testes and from human follicular fluid, can be used for regulating the meiosis in ovocytes and in male germ cells.(FR) Certains composés, structurellement apparentés à des composés naturels susceptibles d'être extraits notamment des testicules de taureau et du liquide folliculaire chez l'homme, sont utilisables pour réguler la méiose dans les ovocytes et les cellules germinales mâles.