methyl 6-((N-((pyridine-2-yl)methyl)benzamido)methyl)pyridine-3-carboxylate | 1402045-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 6-((N-((pyridine-2-yl)methyl)benzamido)methyl)pyridine-3-carboxylate
• 英文别名: Methyl 6-[[benzoyl(pyridin-2-ylmethyl)amino]methyl]pyridine-3-carboxylate；methyl 6-[[benzoyl(pyridin-2-ylmethyl)amino]methyl]pyridine-3-carboxylate
• CAS: 1402045-98-0
• 化学式: C₂₁H₁₉N₃O₃
• 分子量: 361.4
• InChiKey: WMZLSGMRHFKIJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl 6-((N-((pyridine-2-yl)methyl)benzamido)methyl)pyridine-3-carboxylate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 24.0h， 以75%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：

  6-甲基烟酸甲酯 在 碘 、 三乙酰氧基硼氢化钠 、 碘代叔丁烷 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 21.5h， 生成 methyl 6-((N-((pyridine-2-yl)methyl)benzamido)methyl)pyridine-3-carboxylate
  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

• Modification and Optimization of the Bis-picolylamide-Based Relay Protection for Carboxylic Acids to be Cleaved by Unusual Complexation with Cu²⁺ Salts
  作者：Stephan Mundinger、Uwe Jakob、Plamen Bichovski、Willi Bannwarth

  DOI：10.1021/jo301349t

  日期：2012.10.19

  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.