N,N-diethyl-3,4,5-trimethoxy-2-phenylbenzamide | 220805-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-diethyl-3,4,5-trimethoxy-2-phenylbenzamide
• 英文别名: N,N-diethyl-4,5,6-trimethoxy[1,1'-biphenyl]-2-carboxamide
• CAS: 220805-73-2
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: KEUFTCWZEPUCGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3,4,5-trimethoxy-2-phenylbenzamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以51%的产率得到2,3,4-trimethoxyfluorenone
  参考文献：
  名称：

  Stereochemical Variations on the Colchicine Motif. Part 4. A Remote Metalation Approach toward a Colchicine Analog with a Five-Membered B-Ring.

  摘要：

  Attempts to prepare a colchicine analog with a 5-membered B-ring by remote metalation of N,N-diethyl-3,4,5-trimethoxy-2-(5'-methoxy-4'-oxo-2',5',7'-cycloheptatrienyl)-benzamide (2) led to ring contraction of the methoxytropone ring to the p-methoxycarbonylphenyl derivative (3). Dynamic H-1 NMR investigations showed that the biaryl amide 2 exists as a mixture of diastereomers due to hindered rotation around both aryl-aryl and aryl-amide bonds, with rotational barriers of ca. 63 kJ mol(-1). The colchicine and allocolchicine analogs 2 and 3 do not notably affect tubulin polymerization, despite the structural similarities with active analogs. The reduced tubulin binding activity of 2 and 3 may be a result of increasing steric bulk.

  DOI：

  10.3891/acta.chem.scand.52-1380
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 氯化亚砜 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 12.75h， 生成 N,N-diethyl-3,4,5-trimethoxy-2-phenylbenzamide
  参考文献：
  名称：

  钯催化的Ullmann-Ziegler交叉偶联对位阻联芳烃的影响

  摘要：

  我们提出了一种基于改良的Ullmann偶联的简便且通用的联芳基交叉偶联方法，该方法可应用于多种基材。这甚至允许在温和的反应条件下偶联位阻底物。 联芳基-催化-铜-交叉偶联-钯

  DOI：

  10.1055/s-0030-1259968

文献信息

• A Palladium-Catalyzed Ullmann-Ziegler Cross-Coupling for Sterically Hindered Biaryls
  作者：Richard Göttlich、Max Nüllen

  DOI：10.1055/s-0030-1259968

  日期：2011.4

  We present a facile and versatile biaryl cross-coupling procedure based on a modified Ullmann coupling that may be applied to a wide range of substrates. This even allows the coupling of sterically hindered substrates under mild reaction conditions. biaryls - catalysis - copper - cross-coupling - palladium

  我们提出了一种基于改良的Ullmann偶联的简便且通用的联芳基交叉偶联方法，该方法可应用于多种基材。这甚至允许在温和的反应条件下偶联位阻底物。 联芳基-催化-铜-交叉偶联-钯
• Stereochemical Variations on the Colchicine Motif. Part 4. A Remote Metalation Approach toward a Colchicine Analog with a Five-Membered B-Ring.
  作者：Ulf Berg、Håkan Bladh、Berit A. Aanesen、Jacek Stawinski

  DOI：10.3891/acta.chem.scand.52-1380

  日期：——

  Attempts to prepare a colchicine analog with a 5-membered B-ring by remote metalation of N,N-diethyl-3,4,5-trimethoxy-2-(5'-methoxy-4'-oxo-2',5',7'-cycloheptatrienyl)-benzamide (2) led to ring contraction of the methoxytropone ring to the p-methoxycarbonylphenyl derivative (3). Dynamic H-1 NMR investigations showed that the biaryl amide 2 exists as a mixture of diastereomers due to hindered rotation around both aryl-aryl and aryl-amide bonds, with rotational barriers of ca. 63 kJ mol(-1). The colchicine and allocolchicine analogs 2 and 3 do not notably affect tubulin polymerization, despite the structural similarities with active analogs. The reduced tubulin binding activity of 2 and 3 may be a result of increasing steric bulk.