5-Butyl-5-hydroxy-1-methylpyrrolidin-2-one | 165263-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-Butyl-5-hydroxy-1-methylpyrrolidin-2-one
• 英文别名: 5-butyl-5-hydroxy-1-methylpyrrolidin-2-one
• CAS: 165263-86-5
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: QQZOWXRWQOVEAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Butyl-5-hydroxy-1-methylpyrrolidin-2-one 在 盐酸 作用下， 生成 5-butylidene-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides

  摘要：

  SmI2-mediated couplings between a variety of organic halides and cyclic imides have been performed giving either hydroxylactams from N-methylsuccinimide and N-methylphthalimide or delta -ketoamides from N-methylglutarimide. In the latter case, ring opening occurs during hydrolysis. Couplings of imides with alkyl halides require a catalytic amount of NiI2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02148-1
• 作为产物：
  描述：

  N-甲基丁二酰胺 、 1-碘丁烷 在 nickel(II) iodide 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 5-Butyl-5-hydroxy-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides

  摘要：

  SmI2-mediated couplings between a variety of organic halides and cyclic imides have been performed giving either hydroxylactams from N-methylsuccinimide and N-methylphthalimide or delta -ketoamides from N-methylglutarimide. In the latter case, ring opening occurs during hydrolysis. Couplings of imides with alkyl halides require a catalytic amount of NiI2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02148-1

文献信息

• Triflic Anhydride Mediated Cyclization of 5-Hydroxy-Substituted Pyrrolidinones for the Preparation of α-Trifluoromethylsulfonamido Furans
  作者：Albert Padwa、Paitoon Rashatasakhon、Mickea Rose

  DOI：10.1021/jo0341970

  日期：2003.6.1

  (Tf(2)O) in pyridine resulted in the formation of various substituted sulfonamidofurans. The suggested mechanism involves initial formation of an iminium ion which is subsequently transformed into a transient imino triflate. Cyclization of the highly electrophilic imine onto the oxygen atom of the adjacent carbonyl group generates an imino dihydrofuran intermediate. This species reacts further with

  α-当归内酯与烷基胺在水性条件下的反应以高收率得到5-羟基-5-甲基吡咯烷酮。当反应在无水条件下进行时，获得的唯一产物是相应的4-氧戊酸酰胺。用三氟甲磺酸酐（Tf（2）O）在吡啶中处理任一类化合物均导致形成各种取代的磺酰胺基呋喃。所建议的机理涉及亚胺离子的最初形成，其随后被转化为瞬态亚氨基三氟甲磺酸酯。将高度亲电的亚胺环化到相邻羰基的氧原子上，生成亚氨基二氢呋喃中间体。该物质进一步与另一当量的Tf（2）O反应，得到观察到的产物。发现所使用的路易斯酸的性质影响环化反应的结果。在某些情况下，磺酰胺呋喃被用作合成二氢吲哚和相关杂环系统的环加成底物。
• Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides
  作者：Sorin Farcas、Jean-Louis Namy

  DOI：10.1016/s0040-4039(00)02148-1

  日期：2001.1

  SmI2-mediated couplings between a variety of organic halides and cyclic imides have been performed giving either hydroxylactams from N-methylsuccinimide and N-methylphthalimide or delta -ketoamides from N-methylglutarimide. In the latter case, ring opening occurs during hydrolysis. Couplings of imides with alkyl halides require a catalytic amount of NiI2. (C) 2001 Elsevier Science Ltd. All rights reserved.