Benzoic acid (3R,4R)-4-tert-butoxycarbonylamino-1-oxy-4,5-dihydro-3H-pyrrol-3-yl ester | 267234-11-7

• 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: Benzoic acid (3R,4R)-4-tert-butoxycarbonylamino-1-oxy-4,5-dihydro-3H-pyrrol-3-yl ester
• 英文别名: [(3R,4R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxido-3,4-dihydro-2H-pyrrol-1-ium-4-yl] benzoate
• CAS: 267234-11-7
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: LIGIADGTPGERHI-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Benzoic acid (3S,4R)-4-amino-1-benzyl-pyrrolidin-3-yl ester 在 palladium dihydroxide 氢气 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 Benzoic acid (3R,4R)-4-tert-butoxycarbonylamino-1-oxy-4,5-dihydro-3H-pyrrol-3-yl ester
  参考文献：
  名称：

  Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides

  摘要：

  The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02335-7

文献信息

• Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides
  作者：Stefano Cicchi、Paola Ponzuoli、Andrea Goti、Alberto Brandi

  DOI：10.1016/s0040-4039(99)02335-7

  日期：2000.3

  The synthesis of new five-membered enantiopure cyclic nitrones bearing protected cis vicinal amino and hydroxy functionalities is reported. The key step was a Mitsunobu reaction, which allowed placement of an azido group, with inversion of configuration, at the reacting centre. Cycloaddition of the novel nitrones to but-3-en-1-ol followed by simple elaboration of the adducts readily afforded protected amino dihydroxy indolizidines. (C) 2000 Elsevier Science Ltd. All rights reserved.