(4R)-(tert-butyldimethylsilanyloxy)-1-hydroxypyrrolidine-(2S)-carboxylic acid allyl ester | 933469-71-7

• 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: (4R)-(tert-butyldimethylsilanyloxy)-1-hydroxypyrrolidine-(2S)-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxypyrrolidine-2-carboxylate
• CAS: 933469-71-7
• 化学式: C₁₄H₂₇NO₄Si
• 分子量: 301.458
• InChiKey: JALJFDBBVHDYOK-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-(tert-butyldimethylsilanyloxy)-1-hydroxypyrrolidine-(2S)-carboxylic acid allyl ester 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到(7R)-(tert-butyldimethylsilanyloxy)tetrahydro-2,5-dioxa-5a-azacyclopenta[c]pentalene-1-one
  参考文献：
  名称：

  The diastereoselective synthesis of functionalised spirocyclic lactams and lactones using a Cope elimination/intramolecular nitrone cycloaddition strategy

  摘要：

  Functionalised hydroxylamine derivatives of (S)-proline and pipecolic acid have been prepared using a Cope elimination. These hydroxylamines have been found to undergo oxidation to the nitrone either in the presence of air or a catalytic quantity of TPAP. An intramolecular 1,3-dipolar cycloaddition then occurs between the nitrone and pendant double bond to give tricyclic lactams and lactones with high diastereoselectivity. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.046
• 作为产物：
  描述：

  (2S,4R)-1-(2-cyanoethyl)-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 在 2,6-二甲基吡啶 、 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 51.0h， 生成 (4R)-(tert-butyldimethylsilanyloxy)-1-hydroxypyrrolidine-(2S)-carboxylic acid allyl ester
  参考文献：
  名称：

  The diastereoselective synthesis of functionalised spirocyclic lactams and lactones using a Cope elimination/intramolecular nitrone cycloaddition strategy

  摘要：

  Functionalised hydroxylamine derivatives of (S)-proline and pipecolic acid have been prepared using a Cope elimination. These hydroxylamines have been found to undergo oxidation to the nitrone either in the presence of air or a catalytic quantity of TPAP. An intramolecular 1,3-dipolar cycloaddition then occurs between the nitrone and pendant double bond to give tricyclic lactams and lactones with high diastereoselectivity. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.01.046

文献信息

• The diastereoselective synthesis of functionalised spirocyclic lactams and lactones using a Cope elimination/intramolecular nitrone cycloaddition strategy
  作者：Gemma L. Ellis、Ian A. O’Neil、V. Elena Ramos、S. Barret Kalindjian、Alan P. Chorlton、David J. Tapolczay

  DOI：10.1016/j.tetlet.2007.01.046

  日期：2007.3

  Functionalised hydroxylamine derivatives of (S)-proline and pipecolic acid have been prepared using a Cope elimination. These hydroxylamines have been found to undergo oxidation to the nitrone either in the presence of air or a catalytic quantity of TPAP. An intramolecular 1,3-dipolar cycloaddition then occurs between the nitrone and pendant double bond to give tricyclic lactams and lactones with high diastereoselectivity. (c) 2007 Published by Elsevier Ltd.