[(R)-((S)-1-acetyl-2-oxo-cyclopentyl)-furan-2-yl-methyl]-carbamic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: [(R)-((S)-1-acetyl-2-oxo-cyclopentyl)-furan-2-yl-methyl]-carbamic acid methyl ester
• 英文别名: methyl N-[(R)-[(1S)-1-acetyl-2-oxocyclopentyl]-(furan-2-yl)methyl]carbamate
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: CNYCROXIVIMWQW-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基环戊酮 、 (furan-2-ylmethylene)-carbamic acid methyl ester 在 辛可宁 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到[(R)-((S)-1-acetyl-2-oxo-cyclopentyl)-furan-2-yl-methyl]-carbamic acid methyl ester
  参考文献：
  名称：

  Highly Diastereoselective Asymmetric Mannich Reactions of 1,3-Dicarbonyls with Acyl Imines

  摘要：

  The cinchona alkaloids catalyze direct asymmetric Mannich reactions of cyclic 1,3-dicarbonyl compounds with acyl imines to afford a-quaternary carbon-bearing reaction products in yields of up to 98%, a diastereomeric excess of 90% or greater, and enantioselectivities up to 99% ee. A model is proposed that accounts for both the observed diastereoselectivities and the enantioselectivities for the reactions.

  DOI：

  10.1021/ol060304b

文献信息

• [EN] CHIRAL AMINE-CATALYZED ASYMMETRIC ADDITION OF CARBON-CENTERED NUCLEOPHILES TO IMINES<br/>[FR] ADDITION ASYMETRIQUE CATALYSEE PAR UNE AMINE CHIRALE DE NUCLEOPHILES CARBONES SUR DES IMINES
  申请人：UNIV BOSTON

  公开号：WO2007011910A2

  公开（公告）日：2007-01-25

  [EN] The present invention relates to an asymmetric synthesis useful for preparing compounds useful for the treatment of cardiovascular diseases and for studying the role of motor proteins in cell cycle progression.
  [FR] La présente invention porte sur une synthèse asymétrique utilisée pour préparer des composés utilisés servant au traitement de maladies cardiovasculaires et pour étudier le rôle de protéines motrices dans la progression d'un cycle cellulaire.
• Highly Diastereoselective Asymmetric Mannich Reactions of 1,3-Dicarbonyls with Acyl Imines
  作者：Amal Ting、Sha Lou、Scott E. Schaus

  DOI：10.1021/ol060304b

  日期：2006.5.1

  The cinchona alkaloids catalyze direct asymmetric Mannich reactions of cyclic 1,3-dicarbonyl compounds with acyl imines to afford a-quaternary carbon-bearing reaction products in yields of up to 98%, a diastereomeric excess of 90% or greater, and enantioselectivities up to 99% ee. A model is proposed that accounts for both the observed diastereoselectivities and the enantioselectivities for the reactions.