3-Piperidinecarboxylic acid, 2-(4-methoxyphenyl)-6-oxo-1-(phenylmethyl)-, (2R,3R)-rel- | 1943733-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-Piperidinecarboxylic acid, 2-(4-methoxyphenyl)-6-oxo-1-(phenylmethyl)-, (2R,3R)-rel-
• 英文别名: (2S,3S)-1-benzyl-2-(4-methoxyphenyl)-6-oxopiperidine-3-carboxylic acid
• CAS: 1943733-57-0
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: YIEUICZEWBOXGY-PKOBYXMFSA-N

物化性质

• 沸点：
  588.4±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  戊二酸 、 N-苄基-1-(4-甲氧基苯基)甲亚胺 在 乙酸酐 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以70%的产率得到3-Piperidinecarboxylic acid, 2-(4-methoxyphenyl)-6-oxo-1-(phenylmethyl)-, (2R,3R)-rel-
  参考文献：
  名称：

  1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines

  摘要：

  A novel protocol for the Castagnoli-Cushman reaction of dicarboxylic acids and imines comprises the use of 1,1'-carbonyldiimidazole as the cyclodehydrating agent to in situ produce the intermediate anhydrides. In contrast to previously developed procedure involving the use of acetic anhydride, the current protocol allows one to utilize substrates prone to acylation or acid-promoted transformations, which significantly broadens the reaction scope of lactams to be obtained.

  DOI：

  10.1016/j.mencom.2019.05.016

文献信息

• The rare cis-configured trisubstituted lactam products obtained by the Castagnoli–Cushman reaction in N,N-dimethylformamide
  作者：Dmitry Dar'in、Olga Bakulina、Sofia Nikolskaya、Ivan Gluzdikov、Mikhail Krasavin

  DOI：10.1039/c6ra10249b

  日期：——

  trans counterpart, the cis-configured scaffold derived from the Castagnoli–Cushman reaction (CCR) is scarce and has not been explored in bioactive compound design. We found that conducting this reaction in DMF (in contrast to conventional toluene or xylene) led to a significantly higher proportion of cis-configured lactams in the diastereomeric product mixture. This allowed us, for the first time, to obtain

  与它的反式对应物不同，源自Castagnoli-Cushman反应（CCR）的顺式构型支架十分稀少，尚未在生物活性化合物设计中进行探索。我们发现，在DMF中进行该反应（与常规的甲苯或二甲苯相反）导致非对映体产物混合物中的顺式构型内酰胺的比例明显更高。这使我们第一次获得并充分表征了大量铅样CCR内酰胺的两种立体异构体。已经设计了基于1 H NMR的立体化学分配的简单规则，并将其与为纯顺式和反式获得的单晶X射线结构相关-配置的内酰胺。
• 1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines
  作者：Evgeny G. Chupakhin、Olga Yu. Bakulina、Dmitry V. Dar’in、Mikhail Krasavin

  DOI：10.1016/j.mencom.2019.05.016

  日期：2019.5

  A novel protocol for the Castagnoli-Cushman reaction of dicarboxylic acids and imines comprises the use of 1,1'-carbonyldiimidazole as the cyclodehydrating agent to in situ produce the intermediate anhydrides. In contrast to previously developed procedure involving the use of acetic anhydride, the current protocol allows one to utilize substrates prone to acylation or acid-promoted transformations, which significantly broadens the reaction scope of lactams to be obtained.