6-benzyloxyhexanoic acid amide | 874893-89-7

• 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: 6-benzyloxyhexanoic acid amide
• 英文别名: 6-(benzyloxy)hexanamide；6-Phenylmethoxyhexanamide
• CAS: 874893-89-7
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: GBWGZCXLQLUSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-benzyloxyhexanoic acid amide 、 2,7-二氯-1,8-萘啶 在 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 以59%的产率得到2,7-bis(6-benzyloxyhexanoylamino)-1,8-naphthyridine
  参考文献：
  名称：

  Pd-Catalyzed Amidation of 2-Chloro- and 2,7-Dichloro-1,8-naphthyridines

  摘要：

  The catalytic amidation between 2-chloro- and 2,7-dichloro-1,8-naphthyridines and primary amides bearing functional groups is reported. When Pd(OAc)(2), xantphos, and K2CO3 are used, it is possible to obtain symmetric as well as non-symmetric 2,7-diamido-1,8-naphthyridines in 50-90% yield with good functional-group tolerance. Monoamidation of 2,7-dichloro-1,8-naphthyridine using 0.9 equiv of the amide proceeded with good selectivity compared to the formation of the diamide, but as a result of the difficult isolation of the product, isolated yields were poor to moderate (22-42%).

  DOI：

  10.1021/jo051864b
• 作为产物：
  描述：

  6-(benzyloxy)hexanenitrile 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以83%的产率得到6-benzyloxyhexanoic acid amide
  参考文献：
  名称：

  Transition-Metal-Free Hydration of Nitriles Using Potassium tert-Butoxide under Anhydrous Conditions

  摘要：

  Potassium tert-butoxide acts as a nucleophilic oxygen source during the hydration of nitriles to give the corresponding amides under anhydrous conditions. The reaction proceeds smoothly for a broad range of substrates under mild conditions, providing an efficient and economically affordable synthetic route to the amides in excellent yields. This protocol does not need any transition-metal catalyst or any special experimental setup and is easily scalable to bulk scale synthesis. A single-electron-transfer radical mechanism as well as an ionic mechanism have been proposed for the hydration process.

  DOI：

  10.1021/jo502752u

文献信息

• [EN] PROCESS FOR PREPARING INTERMEDIATES<br/>[FR] PROCEDE DE PREPARATION D'INTERMEDIAIRES
  申请人：NOVARTIS AG

  公开号：WO2004026824A1

  公开（公告）日：2004-04-01

  The present invention is directed to a process for preparing intermediates that are useful to prepare certain antibacterial N-formyl hydroxylamine compounds which are peptide deformylase inhibitors. The process makes use α β-lactam intermediate. Certain optically pure intermediates are also claimed.

  本发明涉及一种用于制备中间体的方法，这些中间体对制备某些抗菌N-甲酰羟胺化合物（肽变形酶抑制剂）很有用。该方法利用αβ-内酰胺中间体。还要求某些光学纯中间体。
• BIOLOGICALLY ACTIVE AMINES
  申请人：FISONS plc

  公开号：EP0558677A1

  公开（公告）日：1993-09-08
• PROCESS FOR PREPARING INTERMEDIATES
  申请人：Novartis AG

  公开号：EP1542968A1

  公开（公告）日：2005-06-22
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Polyphor AG

  公开号：EP2499148B1

  公开（公告）日：2017-01-18
• Transition-Metal-Free Hydration of Nitriles Using Potassium <i>tert</i>-Butoxide under Anhydrous Conditions
  作者：Ganesh Chandra Midya、Ajoy Kapat、Subhadip Maiti、Jyotirmayee Dash

  DOI：10.1021/jo502752u

  日期：2015.4.17

  Potassium tert-butoxide acts as a nucleophilic oxygen source during the hydration of nitriles to give the corresponding amides under anhydrous conditions. The reaction proceeds smoothly for a broad range of substrates under mild conditions, providing an efficient and economically affordable synthetic route to the amides in excellent yields. This protocol does not need any transition-metal catalyst or any special experimental setup and is easily scalable to bulk scale synthesis. A single-electron-transfer radical mechanism as well as an ionic mechanism have been proposed for the hydration process.