3α-Isocyanatocholestane | 24281-86-5

• 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
• 英文名称: 3α-Isocyanatocholestane
• 英文别名: 3α-cholestanyl isocyanate；(3R,5S,8R,9S,10S,13R,14S,17R)-3-isocyanato-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 24281-86-5
• 化学式: C₂₈H₄₇NO
• 分子量: 413.687
• InChiKey: NQTOROSHKBQACH-UIALXTEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3α-Isocyanatocholestane 反应 19.0h， 以25 mg的产率得到3α-Acetylamidocholestane
  参考文献：
  名称：

  Stereospecific formation of equatorial diacetylimides from the stereoisomers of six-membered carbocyclic amines

  摘要：

  DOI：

  10.1021/jo00337a055
• 作为产物：
  描述：

  二氧化碳 、 3α-amino-5α-cholestane 在 三丁基膦 、 偶氮二甲酸二异丙酯 作用下， 生成 3α-Isocyanatocholestane
  参考文献：
  名称：

  基于Mitsunobu的方法，可在温和条件下从伯胺和二氧化碳制备烷基和受阻芳基异氰酸酯

  摘要：

  描述了一种基于Mitsunobu的方法，该方法可在非常温和的条件下以优异的产率从伯胺和二氧化碳制备烷基和受阻芳基异氰酸酯。

  DOI：

  10.1016/s0040-4039(98)02312-0

文献信息

• Preparation of Isocyanates from Primary Amines and Carbon Dioxide Using Mitsunobu Chemistry¹
  作者：Dilek Saylik、Michael J. Horvath、Patricia S. Elmes、W. Roy Jackson、Craig G. Lovel、Keith Moody

  DOI：10.1021/jo982362j

  日期：1999.5.1

  Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at -78 degrees C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates gave either carbamoylhydrazines 6 and/or dicarbamoylhydrazines 10 and/or triazolinones 7. The triazolinones were shown to arise from reactions of reactive aryl isocyanates with the Mitsunobu zwitterion. The carbamoylhydrazines were shown not to arise from reaction, of isocyanate with reduced dialkyl azodicarboxylates, and a mechanism for their formation is proposed. Single-crystal X-ray analyses confirmed the structures of 6, 7, and 10.