diethyl (2-tert-butoxycarbonylamino-1-nitro-2-phenylethyl)phosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (2-tert-butoxycarbonylamino-1-nitro-2-phenylethyl)phosphonate
• 英文别名: tert-butyl N-[(1S,2S)-2-[diethoxy(oxido)phosphaniumyl]-2-nitro-1-phenylethyl]carbamate
• 化学式: C₁₇H₂₇N₂O₇P
• 分子量: 402.384
• InChiKey: YSEWACSWWJABLA-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl (2-tert-butoxycarbonylamino-1-nitro-2-phenylethyl)phosphonate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 以63%的产率得到tert-butyl (1R,2R)-2-amino-2-(diethoxyphosphoryl)-1-phenylethylcarbamate
  参考文献：
  名称：

  N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates

  摘要：

  An efficient one-pot synthesis of secondary N-carbamate protected syn-beta-amino-alpha-nitroalkanephosphonates using diethyl nitromethanephosphonate and N-Boc or N-Cbz imines, generated in Situ from stable N-Boc or N-Cbz alpha-aminoalkyl-p-tolylsulfones has been developed under PTC conditions. A model enantioselective version of this reaction is also described. Enantioselectivity up to 67% ee is achieved using a chiral thiourea catalyst derived from a cinchona alkaloid. Completely stereoselective conversion of the title compounds into partially N-carbamate protected syn-1,2-diaminoalkanephosphonates has also been elaborated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.072
• 作为产物：
  描述：

  diethyl (nitromethyl)phosphonate 、 N-[phenyl(toluene-4-sulfonyl)methyl]tert-butoxycarboxyamide 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 26.0h， 以40%的产率得到diethyl (2-tert-butoxycarbonylamino-1-nitro-2-phenylethyl)phosphonate
  参考文献：
  名称：

  N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates

  摘要：

  An efficient one-pot synthesis of secondary N-carbamate protected syn-beta-amino-alpha-nitroalkanephosphonates using diethyl nitromethanephosphonate and N-Boc or N-Cbz imines, generated in Situ from stable N-Boc or N-Cbz alpha-aminoalkyl-p-tolylsulfones has been developed under PTC conditions. A model enantioselective version of this reaction is also described. Enantioselectivity up to 67% ee is achieved using a chiral thiourea catalyst derived from a cinchona alkaloid. Completely stereoselective conversion of the title compounds into partially N-carbamate protected syn-1,2-diaminoalkanephosphonates has also been elaborated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.072

文献信息

• N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates
  作者：Roman Błaszczyk、Anna Gajda、Stefan Zawadzki、Ewelina Czubacka、Tadeusz Gajda

  DOI：10.1016/j.tet.2010.10.072

  日期：2010.12

  An efficient one-pot synthesis of secondary N-carbamate protected syn-beta-amino-alpha-nitroalkanephosphonates using diethyl nitromethanephosphonate and N-Boc or N-Cbz imines, generated in Situ from stable N-Boc or N-Cbz alpha-aminoalkyl-p-tolylsulfones has been developed under PTC conditions. A model enantioselective version of this reaction is also described. Enantioselectivity up to 67% ee is achieved using a chiral thiourea catalyst derived from a cinchona alkaloid. Completely stereoselective conversion of the title compounds into partially N-carbamate protected syn-1,2-diaminoalkanephosphonates has also been elaborated. (C) 2010 Elsevier Ltd. All rights reserved.