4',4'-dimethyl-spiro(5α-cholestane-3,2'-oxazolidine) | 128821-08-9

• 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: 4',4'-dimethyl-spiro(5α-cholestane-3,2'-oxazolidine)
• 英文别名: (5S,8R,9S,10S,13R,14S,17R)-4',4',10,13-tetramethyl-17-[(2R)-6-methylheptan-2-yl]spiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-oxazolidine]
• CAS: 128821-08-9
• 化学式: C₃₁H₅₅NO
• 分子量: 457.784
• InChiKey: XPJQLYFLPHULDM-LJGTUOGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4',4'-dimethyl-spiro(5α-cholestane-3,2'-oxazolidine) 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以68%的产率得到(3-spiro-[2'-N-oxyl-3',3'-dimethyloxazolidine])-5α-cholestane
  参考文献：
  名称：

  Inhibition of in vitro lipid peroxidation by stable steroidic nitroxyl radicals

  摘要：

  4',4'-dimethylspiro (5 alpha-cholestane-3,2'-oxazolidin)-3'-yloxy (IK-1) and 7 alpha,12 alpha-dihydroxy-4',4'-dimethylspiro (5 beta-cholan-24-oic-3,2'-oxazolidin)-3'-yloxy acid (IK-2), two stable steroidic nitroxyl radicals, were newly synthesized and tested as possible inhibitors of lipid peroxidation, induced by. Fenton's reagent in both rat liver microsomes and egg phosphatidylcholine liposomes. The inhibitory activity, evaluated through the formation of thiobarbituric acid reactive substances (TBARS) and the conjugated diene, was compared with that of alpha-tocopherol and 2,2,6,6-tetramethylpiperidine-1-yloxy (TEMPO). In each model system IK-1 and IK-2 exhibited an IC50 of 8 mu M and reduced the formation of TBARS and conjugated diene, showing IK-1 a potency comparable to alpha-tocopherol and higher than TEMPO. Moreover IK-1 and, to a lesser extent IK-2, reduced the lipid peroxidation induced in the microsomes by the water-soluble azo-initiator 2,2'-Azobis (2-methylpropionamidine) dihydrochloride (AMPH), indicating the IK-1 and IK-2 ability as chain-breaking antioxidants. The hydroxylamine 4',4'-dimethylspiro (5 alpha-cholestane-3,2'-oxazolidin)-3'-hydroxide (IK-3), obtained by chemical reduction of IK-1, was completely inactive as an inhibitor of lipid peroxidation in heat pre-treated microsomes and in liposomes. However in microsomes it was active since it was oxidized to the corresponding nitroxyl radical IK-1. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00052-2
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 、 2-氨基-2-甲基-1-丙醇 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以0.39 g的产率得到4',4'-dimethyl-spiro(5α-cholestane-3,2'-oxazolidine)
  参考文献：
  名称：

  乙酸铵作为空间位阻官能化羟胺与酮缩合的催化剂

  摘要：

  发现乙酸铵是 α-羟基氨基肟和 α-羟基氨基醇与酮缩合的催化剂。这种缩合导致空间位阻杂环羟胺，它是稳定的氮氧化合物的前体。

  DOI：

  10.1007/bf02502943

文献信息

• Murray, Robert W.; Singh, Megh, Synthetic Communications, 1989, vol. 19, # 20, p. 3509 - 3522
  作者：Murray, Robert W.、Singh, Megh

  DOI：——

  日期：——
• US5087752A
  申请人：——

  公开号：US5087752A

  公开（公告）日：1992-02-11