(1R,2S)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclopent-3-enecarboxylic acid methyl ester | 1029540-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclopent-3-enecarboxylic acid methyl ester
• 英文别名: methyl (1R,2S)-2-(hydroxymethyl)-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-3-ene-1-carboxylate
• CAS: 1029540-04-2
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: IDLNGXWWGASXFE-NOZJJQNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclopent-3-enecarboxylic acid methyl ester 、 (-)-(R)-α-methoxy-α-(9-anthryl)acetic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (1R,2S)-2-(((R)-2-(anthracen-9-yl)-2-methoxyacetoxy)methyl)-1-((tert-butoxycarbonyl)amino)cyclopent-3-ene-1-carboxylate
  参考文献：
  名称：

  Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence

  摘要：

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.

  DOI：

  10.1021/jo800496h
• 作为产物：
  描述：

  (1R,2S)-1-(tert-butoxycarbonylamino)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopent-3-enecarboxylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到(1R,2S)-1-(tert-butoxycarbonylamino)-2-(hydroxymethyl)cyclopent-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence

  摘要：

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.

  DOI：

  10.1021/jo800496h

文献信息

• Directed Diastereoselectivity in the Asymmetric Claisen/Metathesis Reaction Sequence
  作者：Nicolas P. Probst、Arnaud Haudrechy、Karen Plé

  DOI：10.1021/jo800496h

  日期：2008.6.1

  The Claisen/metathesis sequence is a versatile synthetic tool for the synthesis of quaternary hydroxy and amino acid carbocycles. By correctly choosing both the configuration of the allylic alcohol and the double bond geometry, specific access to any one of four possible stereoisomers is possible in good yield and excellent diastereoselectivity. The enantiomerically pure allylic alcohols are easily obtained by addition of terminal alkynes to aldehydes. Controlled reduction of the triple bond then gives the desired double bond geometry.