tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate | 1291083-47-0

• 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: tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate
• 英文别名: tert-butyl N-[(1R,2S)-5-[tert-butyl(dimethyl)silyl]oxy-2-nitro-1-phenylpentyl]carbamate
• CAS: 1291083-47-0
• 化学式: C₂₂H₃₈N₂O₅Si
• 分子量: 438.64
• InChiKey: MTGFQKZLCHWZNR-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate 在 四丁基氟化铵 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到tert-butyl (1R,2S)-5-hydroxy-2-nitro-1-phenylpentylcarbamate
  参考文献：
  名称：

  A concise enantioselective synthesis of l-(−)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate using catalytic enantioselective aza-Henry reaction as key step

  摘要：

  An efficient enantioselective synthesis of L-(-)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate is accomplished by means of catalytic enantioselective aza-Henry reaction. A key feature of this protocol is organocatalysis as genesis of chirality to ensure high degree of distereo- and enantiocontrol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.031
• 作为产物：
  描述：

  N-[phenyl(toluene-4-sulfonyl)methyl]tert-butoxycarboxyamide 、 tert-butyl(dimethyl)(4-nitrobutoxy)silane 在 cesiumhydroxide monohydrate 、 N-benzylquininium chloride 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 tert-butyl (1R,2S)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate 、 tert-butyl (1S,2S)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate 、 tert-butyl (1R,2R)-5-(tert-butyldimethylsilyloxy)-2-nitro-1-phenylpentylcarbamate
  参考文献：
  名称：

  A concise enantioselective synthesis of l-(−)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate using catalytic enantioselective aza-Henry reaction as key step

  摘要：

  An efficient enantioselective synthesis of L-(-)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate is accomplished by means of catalytic enantioselective aza-Henry reaction. A key feature of this protocol is organocatalysis as genesis of chirality to ensure high degree of distereo- and enantiocontrol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.031

文献信息

• A concise enantioselective synthesis of l-(−)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate using catalytic enantioselective aza-Henry reaction as key step
  作者：Gullapalli Kumaraswamy、Arigala Pitchaiah

  DOI：10.1016/j.tet.2011.02.031

  日期：2011.4

  An efficient enantioselective synthesis of L-(-)-733,061 and (2S,3S)-methyl 3-aminopiperidine-2-carboxylate is accomplished by means of catalytic enantioselective aza-Henry reaction. A key feature of this protocol is organocatalysis as genesis of chirality to ensure high degree of distereo- and enantiocontrol. (C) 2011 Elsevier Ltd. All rights reserved.