N-(tetrahydrofuran-2-yl)-1H-indole | 50640-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(tetrahydrofuran-2-yl)-1H-indole
• 英文别名: 1-(Tetrahydrofuran-2-yl)-1H-indole；1-(oxolan-2-yl)indole
• CAS: 50640-00-1
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: UTEDPNLNJBYVSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  4-羟基-1-(1H-吲哚-1-基)-1-丁烷硫酮 在 trimethoxonium tetrafluoroborate 、 sodium tetrahydroborate 作用下， 以 乙腈 为溶剂， 反应 1.08h， 以61%的产率得到N-(tetrahydrofuran-2-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of N‐Glycoside Analogs via Thionolactones

  摘要：

  Indolyl N-glycoside analogs were obtained by a two-step sequence via indole N-thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N-thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N- over C3-acylation. Treatment of the omega-hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N-(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the omega-hydroxyl group can give access to tetrahydrothiophene N-glycosides.

  DOI：

  10.1081/car-120026472

文献信息

• Copper-Catalyzed Oxidative Dehydrogenative C(sp³ )−H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources
  作者：Chang-Sheng Wang、Xiao-Feng Wu、Pierre H. Dixneuf、Jean-François Soulé

  DOI：10.1002/cssc.201700783

  日期：2017.8.10

  A copper-catalyzed oxidative C(sp3)−H/N−H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)−N bond formation through a radical pathway generated by homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerates a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile

  已经开发出铜-NH-杂环与可负担的（环）烷烃的氧化C（sp 3）-H / N-H偶联。该程序涉及通过自由基途径形成C（sp 3）-N键，该自由基途径是由二叔丁基过氧化物的均相裂解和铜催化剂捕获自由基而产生的。该反应可耐受一系列官能团，例如溴，氟，酯，酮，腈，甲基和甲氧基。游离的含NH的吲哚，吡咯，吡唑，吲唑和苯并三唑已成功进行N烷基化。
• Transition Metal-Free Intermolecular α-CH Amination of Ethers at Room Temperature
  作者：Ivan Buslov、Xile Hu

  DOI：10.1002/adsc.201400646

  日期：2014.11.3

  AbstractWe describe a new method for the intermolecular amination of the α‐CH bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti‐cancer prodrug Tegafur and its analogues.magnified image
• Reaction of 3-[2'-tetrahydropyranyl(furanyl)thio]indole with silver ion
  作者：Terry D. Lee、Michael V. Pickering、G. Doyle Daves

  DOI：10.1021/jo00922a020

  日期：1974.4
• Synthesis of <i>N</i>‐Glycoside Analogs via Thionolactones
  作者：Wendong Wang、Pornpun Rattananakin、Peter G. Goekjian

  DOI：10.1081/car-120026472

  日期：2003.12.31

  Indolyl N-glycoside analogs were obtained by a two-step sequence via indole N-thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N-thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N- over C3-acylation. Treatment of the omega-hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N-(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the omega-hydroxyl group can give access to tetrahydrothiophene N-glycosides.