N-Methyl-4-(thiophene-2-yl)butyramide | 165532-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-Methyl-4-(thiophene-2-yl)butyramide
• 英文别名: N-methyl-4-thiophen-2-ylbutanamide
• CAS: 165532-49-0
• 化学式: C₉H₁₃NOS
• mdl: MFCD19595539
• 分子量: 183.274
• InChiKey: UJLXWGCJCUEANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Methyl-4-(thiophene-2-yl)butyramide 在 六甲基磷酰三胺 、 正丁基锂 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 3.17h， 生成 2-Diazo-N-<(4-thiophene-2-yl)butyryl>-N-methyl-3-oxobutyramide
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037
• 作为产物：
  描述：

  4-(thiophen-2-yl)butanenitrile 在 氢氧化钾 、 N,N'-羰基二咪唑 作用下， 以 乙醇 为溶剂， 反应 25.5h， 生成 N-Methyl-4-(thiophene-2-yl)butyramide
  参考文献：
  名称：

  Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic .pi.-Systems

  摘要：

  A series of furanyl-, thienyl-, and indole-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom. The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomunchnones across a tethered furan and thiophene ring were studied. The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities. The reaction is critically dependent on conformational factors in the transition state. In addition, the first examples of intramolecular cycloaddition of isomunchnones to indole dipolarophiles are reported. Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.

  DOI：

  10.1021/jo00102a037

文献信息

• METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica NV

  公开号：EP1332133B1

  公开（公告）日：2008-07-09
• US5846990A
  申请人：——

  公开号：US5846990A

  公开（公告）日：1998-12-08
• US7517517B2
  申请人：——

  公开号：US7517517B2

  公开（公告）日：2009-04-14
• US7629468B2
  申请人：——

  公开号：US7629468B2

  公开（公告）日：2009-12-08
• [EN] RADIOLABELLED QUINOLINE AND QUINOLINONE DERIVATIVES AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR LIGANDS<br/>[FR] DERIVES RADIOMARQUES DE QUINOLINE ET DE QUINOLINONE ET LEUR UTILISATION EN TANT QUE LIGANDS DU RECEPTEUR METABOTROPIQUE DU GLUTAMATE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2003082350A2

  公开（公告）日：2003-10-09

  The present invention is concerned with radiolabelled quinoline and quinolinone derivatives according Formula (I-A)* or (I-B)* showing metabotropic glutamate receptor antagonistic activity, in particular mGlu1 receptor activity, and their preparation ; it further relates to compositions comprising them, as well as their use for marking and identifying metabotropic glutamate receptor sites and for imaging an organ. In a preferable embodiment, X represents O; R1 represents C1-6alkyl; cyclo3-12alkyl or (cycloC3-12alkyl)C1-6alkyl, wherein one or more hydrogen atoms in a C1-6alkyl-moiety or in a cycloC3-12alkyl-moiety optionally may be replaced by C1-6alkyloxy, aryl, halo or thienyl; R2 represents hydrogen; halo; C1-6alkyl or amino; R3 and R4 each independently represent hydrogen or C1-6alkyl; or R2 and R3 may be taken together to form -R2-R3-, which represents a bivalent radical of formula -Z4-CH2-CH2-CH2- or -Z4-CH2-CH2- with Z4 being O or NR11 wherein R11 is C1-6alkyl; and wherein each bivalent radical is optionally substituted with C1-6alkyl; or R3 and R4 may be taken together to form a bivalent radical of formula -CH2-CH2-CH2-CH2- ; R5 represents hydrogen; Y represents O; and aryl represents phenyl optionally substituted with halo. Most preferred are radiolabelled compounds in which the radioactive isotope is selected from the group of of 3H, 11C and 18F. The invention also relates to their use in a diagnostic method, in perticular for marking and identifying a mGluR1 receptor in biological material, as well as to their use for imaging an organ, in particular using PET.