(4R,5R)-4,5-di-tert-butylimidazolidin-2-imine | 1130601-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4R,5R)-4,5-di-tert-butylimidazolidin-2-imine
• 英文别名: (4R,5R)-4,5-ditert-butyl-4,5-dihydro-1H-imidazol-2-amine
• CAS: 1130601-50-1
• 化学式: C₁₁H₂₃N₃
• 分子量: 197.324
• InChiKey: PYVDSEPORUXKQR-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴化氰 、 (1R,2R)-1,2-diaminocyclohexane 以 乙腈 为溶剂， 反应 48.0h， 以99%的产率得到(4R,5R)-4,5-di-tert-butylimidazolidin-2-imine
  参考文献：
  名称：

  Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction

  摘要：

  A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst Structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine variants. These compounds were applied to the aza-Henry reaction between N-Boc imines and nitroalkanes generating the beta-nitroamines in up to 77% ee and up to 20:1 diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.058
• 作为试剂：
  描述：

  硝基丙烷 、 tert-butyl benzylidenecarbamate 在 (4R,5R)-4,5-di-tert-butylimidazolidin-2-imine 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (1S,2S)-2-nitro-1-phenylbutylcarbamic acid tert-butyl ester 、 tert-butyl [(1S,2R)-2-nitro-1-phenylbutyl]carbamate 、 tert-butyl (1R,2S)-2-nitro-1-phenylbutylcarbamate 、 (1R,2R)-2-nitro-1-phenylbutylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction

  摘要：

  A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst Structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine variants. These compounds were applied to the aza-Henry reaction between N-Boc imines and nitroalkanes generating the beta-nitroamines in up to 77% ee and up to 20:1 diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.058

文献信息

• Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction
  作者：Helena M. Lovick、Forrest E. Michael

  DOI：10.1016/j.tetlet.2008.12.058

  日期：2009.3

  A series of chiral guanidines were synthesized and shown to efficiently catalyze the aza-Henry reaction. Modifications of the catalyst Structure revealed important selectivity trends as well as an intriguing reversal in stereoselectivity with bisguanidine variants. These compounds were applied to the aza-Henry reaction between N-Boc imines and nitroalkanes generating the beta-nitroamines in up to 77% ee and up to 20:1 diastereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.