5α-hydroxy-6β-[2-hydroxyethylamino]-cholestan-3β-ol | 1379475-27-0

• 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: 5α-hydroxy-6β-[2-hydroxyethylamino]-cholestan-3β-ol
• 英文别名: 5alpha-Hydroxy-6beta-[2-hydroxyethylamino]-cholestan-3beta-ol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-(2-hydroxyethylamino)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5-diol
• CAS: 1379475-27-0
• 化学式: C₂₉H₅₃NO₃
• 分子量: 463.745
• InChiKey: YPBFWCWPCNSPIC-OYYJYTPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C.I.酸性橙108 、 胆固醇-5Alpha,6Alpha-环氧化物 以 正丁醇 为溶剂， 反应 40.0h， 以98%的产率得到5α-hydroxy-6β-[2-hydroxyethylamino]-cholestan-3β-ol
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF STEROL DERIVATIVES
  [FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS DE STÉROL

  摘要：

  本发明涉及一种用于制备甾醇衍生物的方法，包括在含有3至5个碳原子的醇溶剂中，将α-环氧化合物与胺反应的过程。

  公开号：

  WO2013076257A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF STEROL DERIVATIVES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS DE STÉROL
  申请人：INST NAT SANTE RECH MED

  公开号：WO2013076257A1

  公开（公告）日：2013-05-30

  The present invention relates to a process for the preparation of sterol derivatives comprising the reaction of an α-epoxy compound with an amine in an alcohol comprising 3 to 5 carbon atoms as a solvent.

  本发明涉及一种用于制备甾醇衍生物的方法，包括在含有3至5个碳原子的醇溶剂中，将α-环氧化合物与胺反应的过程。
• PROCESS FOR THE PREPARATION OF STEROL DERIVATIVES
  申请人：INSERM (Institut National de la Sante et de la Recherche Medicale)

  公开号：US20140309417A1

  公开（公告）日：2014-10-16

  The present invention relates to a process for the preparation of sterol derivatives comprising the reaction of an α-epoxy compound with an amine in an alcohol comprising 3 to 5 carbon atoms as a solvent.

  本发明涉及一种制备甾醇衍生物的方法，包括在一种含有3至5个碳原子的醇作为溶剂的情况下，将α-环氧化合物与胺反应。
• Process for the preparation of sterol derivatives
  申请人：INSERM (Institut National de la Sante et de la Recherche Medicale)

  公开号：US09447141B2

  公开（公告）日：2016-09-20

  The present invention relates to a process for the preparation of sterol derivatives comprising the reaction of an α-epoxy compound with an amine in an alcohol comprising 3 to 5 carbon atoms as a solvent.

  本发明涉及一种制备甾醇衍生物的方法，其中将α-环氧化合物与一种胺在含有3到5个碳原子的醇类溶剂中进行反应。
• US9447141B2
  申请人：——

  公开号：US9447141B2

  公开（公告）日：2016-09-20
• Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles
  作者：Michael R. Paillasse、Nathalie Saffon、Heinz Gornitzka、Sandrine Silvente-Poirot、Marc Poirot、Philippe de Medina

  DOI：10.1194/jlr.m023689

  日期：2012.4

  We recently established that drugs used for the treatment and the prophylaxis of breast cancers, such as tamoxifen, were potent inhibitors of cholesterol-5,6-epoxide hydrolase (ChEH), which led to the accumulation of 5,6 alpha-epoxy-cholesterol (5,6 alpha-EC) and 5,6 beta-epoxy-cholesterol (5,6 beta-EC). This could be considered a paradox because epoxides are known as alkylating agents with putative carcinogenic properties. We report here that, as opposed to the carcinogen styrene-oxide, neither of the ECs reacted spontaneously with nucleophiles. Under catalytic conditions, 5,6 beta-EC remains unreactive whereas 5,6 alpha-EC gives cholestan-3 beta,5 alpha-diol-6 beta-substituted compounds. These data showed that 5,6-ECs are stable epoxides and unreactive toward nucleophiles in the absence of a catalyst, which contrasts with the well-known reactivity of aromatic and aliphatic epoxides.(jlr) These data rule out 5,6-EC acting as spontaneous alkylating agents. In addition, these data support the existence of a stereoselective metabolism of 5,6 alpha-EC.-Paillasse, M. R., N. Saffon, H. Gornitzka, S. Silvente-Poirot, M. Poirot, and P. de Medina. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. J. Lipid Res. 2012. 53: 718-725.