2-Furyl (α-phenylamino)benzyl ketone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Furyl (α-phenylamino)benzyl ketone
• 英文别名: 2-Anilino-1-(furan-2-yl)-2-phenylethanone
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: JSGFUOIVMKNPBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(三甲基硅)苯基三氟甲烷磺酸盐 、 2-Furyl (α-phenylamino)benzyl ketone 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  通过芳烃和α-氨基酮的反应无过渡金属合成多取代的N-芳基吲哚

  摘要：

  使用芳烃环加成反应已开发出一种简单的无过渡金属合成吲哚的方法。在温和条件下，通过一步N-芳基化-亲核加成过程，原位生成的芳烃与α-氨基酮偶联，并有效地生产出多取代的N-芳基吲哚。

  DOI：

  10.1016/j.tet.2014.02.028
• 作为产物：
  描述：

  2-糠醛缩二乙醇 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 4.03h， 生成 2-Furyl (α-phenylamino)benzyl ketone
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

  摘要：

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.

  DOI：

  10.1021/jo00128a039

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• KETONES
  申请人：AstraZeneca AB

  公开号：EP1549600A1

  公开（公告）日：2005-07-06
• Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
  作者：Alan R. Katritzky、Hengyuan Lang、Zuoquan Wang、Zhongxing Zhang、Huimin Song

  DOI：10.1021/jo00128a039

  日期：1995.11

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.
• Transition-metal-free synthesis of multisubstituted N-arylindoles via reaction of arynes and α-amino ketones
  作者：Lin He、Ji-Xin Pian、Jun-Feng Shi、Guang-Fen Du、Bin Dai

  DOI：10.1016/j.tet.2014.02.028

  日期：2014.4

  A simple transition-metal-free protocol for the synthesis of indoles has been developed using aryne cycloaddition. The in situ-generated arynes couple with α-amino ketones through a one-step N-arylation–nucleophilic addition process under mild conditions and efficiently produce multisubstituted N-arylindoles.

  使用芳烃环加成反应已开发出一种简单的无过渡金属合成吲哚的方法。在温和条件下，通过一步N-芳基化-亲核加成过程，原位生成的芳烃与α-氨基酮偶联，并有效地生产出多取代的N-芳基吲哚。