3β-cholestanyloxy methane thiol | 98569-96-1

• 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: 3β-cholestanyloxy methane thiol
• 英文别名: O-cholestanyl-O'-methylenethiol
• CAS: 98569-96-1
• 化学式: C₂₈H₅₀OS
• 分子量: 434.77
• InChiKey: SGXRFYZKYRMZIT-PGAJIAHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-(5α-cholestan-3β-yloxythiocarbonyl)imidazole 在 偶氮二异丁腈 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 生成 3β-cholestanyloxy methane thiol
  参考文献：
  名称：

  三丁基锡烷还原二硫代碳酸酯（黄原酸酯）的机理

  摘要：

  各种二硫代碳酸酯的竞争实验表明，脱氧反应是通过添加苯乙烯基自由基生成（2），然后进行裂解，而不是直接对硫化物硫进行S H 2攻击而进行的。

  DOI：

  10.1039/c39850000646

文献信息

• The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry
  作者：Derek H.R. Barton、Doo Ok Jang、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4020(01)87198-2

  日期：1993.8

  Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.

  各种thionocarbonates和醇的黄原酸盐和二的-xanthates VIC -diols容易脱氧成相应的烃或烯烃，而溴化物和碘化物与以良好的收率diphenylphenylsilane脱卤。
• On the mechanism of the deoxygenation of secondary alcohols by the reduction of their methyl xanthates by tin hydrides
  作者：Derek H.R. Barton、David Crich、Antonius Löbberding、Samir Z. Zard

  DOI：10.1016/s0040-4020(01)90614-3

  日期：1986.1

  Two alternate proposals for the mechanism of reduction of xanthates by tributylstannane have been examined. Evidence has been secured that under normal reduction conditions the thiocarbonyl group is attacked reversibly. At a high enough temperature the carbon radical fragments to give eventually the reduction product. Under modified conditions, where no reducing agent (Sn-H) is present, the radical

  研究了关于通过三丁基锡烷还原黄药的两种替代方案。有证据表明，在正常还原条件下，硫羰基可逆地被攻击。在足够高的温度下，碳自由基断裂以最终产生还原产物。在改性条件下，不存在还原剂（Sn-H）时，形成的自由基消除了甲基硫代三丁基锡，并提供了在esr光谱中观察到的硫代羰氧基基团。
• On the mechanism of deoxygenation of secondary alcohols by tin hydride reduction of methyl xanthates and other thiocarbonyl derivatives
  作者：Derek H.R. Barton、Jang Doo Ok、Joseph Cs. Jaszberenyi

  DOI：10.1016/s0040-4039(00)94480-0

  日期：1990.1

  The room temperature deoxygenation of xanthates and thionocarbonates using (n-Bu) 3Sn-H — Et3B — air has been studied, especially with 119Sn N.M.R. spectroscopy. The original conception of tin radical attack on thiocarbonyl is confirmed.

  使用（n -Bu ）3 Sn-H-Et 3 B-空气对黄原酸酯和硫代碳酸酯的室温脱氧进行了研究，尤其是利用119 Sn NMR光谱。锡自由基攻击硫代羰基的最初概念得到证实。