N-(2-dimethylaminoethyl)-N-pyridin-2-ylmethylbenzamide | 1402045-88-8

• 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-(2-dimethylaminoethyl)-N-pyridin-2-ylmethylbenzamide
• 英文别名: N-(2-dimethylaminoethyl)-N-pyridine-2-ylmethylbenzamide；N-[2-(dimethylamino)ethyl]-N-(pyridin-2-ylmethyl)benzamide
• CAS: 1402045-88-8
• 化学式: C₁₇H₂₁N₃O
• 分子量: 283.373
• InChiKey: XJDHUVPYIVRFHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(2-dimethylaminoethyl)-N-pyridin-2-ylmethylbenzamide 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 24.0h， 以100%的产率得到苯甲酸甲酯
  参考文献：
  名称：

  Modification and Optimization of the Bis-picolylamide-Based Relay Protection for Carboxylic Acids to be Cleaved by Unusual Complexation with Cu²⁺ Salts

  摘要：

  A simple modification of our recently published protection scheme for carboxylic acids as amides resulted in a new protecting group with significantly improved properties. It requires shorter reaction times for deprotection and allows us to replace Cu(OTf)(2) by CuCl2, indicating at the same time the importance of the nature of the anion of the Cu2+ source. Since the new scheme fulfills all criteria required for an ideal protection group it should find widespread application in synthetic organic chemistry.

  DOI：

  10.1021/jo301349t
• 作为产物：
  描述：

  吡啶-2-甲醛 在 三乙酰氧基硼氢化钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 18.17h， 生成 N-(2-dimethylaminoethyl)-N-pyridin-2-ylmethylbenzamide
  参考文献：
  名称：

  Modification and Optimization of the Bis-picolylamide-Based Relay Protection for Carboxylic Acids to be Cleaved by Unusual Complexation with Cu²⁺ Salts

  摘要：

  A simple modification of our recently published protection scheme for carboxylic acids as amides resulted in a new protecting group with significantly improved properties. It requires shorter reaction times for deprotection and allows us to replace Cu(OTf)(2) by CuCl2, indicating at the same time the importance of the nature of the anion of the Cu2+ source. Since the new scheme fulfills all criteria required for an ideal protection group it should find widespread application in synthetic organic chemistry.

  DOI：

  10.1021/jo301349t

文献信息

• Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions
  作者：Stephan Mundinger、Uwe Jakob、Willi Bannwarth

  DOI：10.1002/chem.201302708

  日期：2014.1.27

  conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise

  已经开发了基于螯合胺的三个结构上相关的羧酸中继保护基。这些保护基可以很容易地通过在2-（1 H-苯并三唑-1-基）-1,1,3,3-四甲基溴化四氟硼酸盐（TBTU）。这些保护基除了对整个反应条件稳定外，在酸性和碱性条件下也稳定，因此可以与羧酸的酯保护剂结合使用。这些保护基的裂解被金属离子的螯合激活，这涉及酰胺氮的异常配位。尽管它们相似，但是通过施加不同的金属盐，可以逐步和正交方式裂解这些保护基。