N',N'-dibenzyl-2,4,5-trifluoro-3-methoxybenzohydrazide

• 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'-dibenzyl-2,4,5-trifluoro-3-methoxybenzohydrazide
• 化学式: C₂₂H₁₉F₃N₂O₂
• 分子量: 400.4
• InChiKey: IMYCJUZTBKYOLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N',N'-dibenzyl-2,4,5-trifluoro-3-methoxybenzohydrazide 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-cyclopropyl-1-(dibenzylamino)-1-(2,4,5-trifluoro-3-methoxybenzoyl)urea
  参考文献：
  名称：

  The Preparation of Two, Preclinical Amino-quinazolinediones as Antibacterial Agents

  摘要：

  This paper describes the synthesis of two amino-quinazolinediones which are potent gyrase/topoisomerase inhibitors and useful as antibacterial agents. The early scale-up work to prepare a chiral side chain on multigram scale and two different amino-quinazolinedione cores is detailed. The enabling synthesis for the side chain employed a previously reported Michael addition of MeNO2 to an enantiomerically enriched delta-amino-enoate and a two-step de-oxygenation of a lactam. Key synthetic steps for core preparation and completion of the amino-quinazolinediones include dianion-promoted cyclization via intramolecular, nucleophilic aromatic substitution, electrophilic amination, nucleophilic aromatic substitution of the side chain to the core, deprotection and isolation of the hydrochloride salt in acceptable yield.

  DOI：

  10.1021/op7000639
• 作为产物：
  描述：

  3-甲氧基-2,4,5-三氟苯甲酸 、 1,1-二苄肼 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N',N'-dibenzyl-2,4,5-trifluoro-3-methoxybenzohydrazide
  参考文献：
  名称：

  The Preparation of Two, Preclinical Amino-quinazolinediones as Antibacterial Agents

  摘要：

  This paper describes the synthesis of two amino-quinazolinediones which are potent gyrase/topoisomerase inhibitors and useful as antibacterial agents. The early scale-up work to prepare a chiral side chain on multigram scale and two different amino-quinazolinedione cores is detailed. The enabling synthesis for the side chain employed a previously reported Michael addition of MeNO2 to an enantiomerically enriched delta-amino-enoate and a two-step de-oxygenation of a lactam. Key synthetic steps for core preparation and completion of the amino-quinazolinediones include dianion-promoted cyclization via intramolecular, nucleophilic aromatic substitution, electrophilic amination, nucleophilic aromatic substitution of the side chain to the core, deprotection and isolation of the hydrochloride salt in acceptable yield.

  DOI：

  10.1021/op7000639

文献信息

• The Preparation of Two, Preclinical Amino-quinazolinediones as Antibacterial Agents
  作者：Vladimir Beylin、David C. Boyles、Timothy T. Curran、Dainius Macikenas、Parlett、Derek Vrieze

  DOI：10.1021/op7000639

  日期：2007.5.1

  This paper describes the synthesis of two amino-quinazolinediones which are potent gyrase/topoisomerase inhibitors and useful as antibacterial agents. The early scale-up work to prepare a chiral side chain on multigram scale and two different amino-quinazolinedione cores is detailed. The enabling synthesis for the side chain employed a previously reported Michael addition of MeNO2 to an enantiomerically enriched delta-amino-enoate and a two-step de-oxygenation of a lactam. Key synthetic steps for core preparation and completion of the amino-quinazolinediones include dianion-promoted cyclization via intramolecular, nucleophilic aromatic substitution, electrophilic amination, nucleophilic aromatic substitution of the side chain to the core, deprotection and isolation of the hydrochloride salt in acceptable yield.