(5S)-5-Benzyl-N-tosylpyrrolidin-3-one | 249298-03-1

• 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: (5S)-5-Benzyl-N-tosylpyrrolidin-3-one
• 英文别名: (5S)-5-benzyl-1-(4-methylphenyl)sulfonylpyrrolidin-3-one
• CAS: 249298-03-1
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: CXMIEYOEBNBTEY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-Benzyl-N-tosylpyrrolidin-3-one 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到(S)-4-Benzyl-3-(toluene-4-sulfonyl)-[1,3]oxazinan-6-one
  参考文献：
  名称：

  Regioselective Baeyer–Villiger lactonization of 2-substituted pyrrolidin-4-one. Synthesis of statine

  摘要：

  Nine 2-substituted pyrrolidin-4-ones 4a-i were obtained via a series of functional group transformation of known prolinol 5 by facile six kinds of methodologies. The target structure of 1,3-amino alcohols 2a-i was constructed in the regioselective Baeyer-Villiger lactonization of ketones 4a-i and reduction of the resulting 4-substituted tetrahydro-1,3-oxazin-6-ones 3a-i. A new and straightforward synthesis of (3S,4S)-statine (6) has been established starting from trans-(2S,4R)-4-hydroxyproline (1). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.027
• 作为产物：
  描述：

  N-[(2S)-5-diazo-4-oxo-1-phenylpentan-2-yl]-4-methylbenzenesulfonamide 在 copper acetylacetonate 作用下， 以 苯 为溶剂， 反应 1.5h， 以61%的产率得到(5S)-5-Benzyl-N-tosylpyrrolidin-3-one
  参考文献：
  名称：

  Intramolecular N–H insertion of α-diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines

  摘要：

  Cu(acac)2被发现是羧烯体催化的分子内N–H插入反应的高效催化剂。在以Cu(acac)2为催化剂的重氮分解反应中，羧烯体的竞争性分子内C–H插入并不是一个问题。该反应以中到好的产率提供了3-氧杂环丁烷、3-氧杂环戊烷和3-氧杂环己烷的衍生物。

  DOI：

  10.1039/a903722e

文献信息

• Intramolecular N–H insertion of α-diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines
  作者：Jianbo Wang、Yihua Hou、Peng Wu

  DOI：10.1039/a903722e

  日期：——

  Cu(acac)2 was found to be an efficient catalyst for the intramolecular N–H insertion by carbenoids. The competitive intramolecular C–H insertion by carbenoids is not a problem in the diazo decomposition reaction with Cu(acac)2 as catalyst. The reaction provided derivatives of 3-oxoazetidine, 3-oxopyrrolidine and 3-oxopiperidine in moderate to good yields.

  Cu(acac)2被发现是羧烯体催化的分子内N–H插入反应的高效催化剂。在以Cu(acac)2为催化剂的重氮分解反应中，羧烯体的竞争性分子内C–H插入并不是一个问题。该反应以中到好的产率提供了3-氧杂环丁烷、3-氧杂环戊烷和3-氧杂环己烷的衍生物。
• Regioselective Baeyer–Villiger lactonization of 2-substituted pyrrolidin-4-one. Synthesis of statine
  作者：Meng-Yang Chang、Yung-Hua Kung、Shui-Tein Chen

  DOI：10.1016/j.tetlet.2006.05.027

  日期：2006.7

  Nine 2-substituted pyrrolidin-4-ones 4a-i were obtained via a series of functional group transformation of known prolinol 5 by facile six kinds of methodologies. The target structure of 1,3-amino alcohols 2a-i was constructed in the regioselective Baeyer-Villiger lactonization of ketones 4a-i and reduction of the resulting 4-substituted tetrahydro-1,3-oxazin-6-ones 3a-i. A new and straightforward synthesis of (3S,4S)-statine (6) has been established starting from trans-(2S,4R)-4-hydroxyproline (1). (c) 2006 Elsevier Ltd. All rights reserved.