(R)-2-(N,N-dibenzylamino)-3-(p-tolylsulfonyl)propanamide | 466671-23-8

• 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: (R)-2-(N,N-dibenzylamino)-3-(p-tolylsulfonyl)propanamide
• 英文别名: (2R)-2-(dibenzylamino)-3-(4-methylphenyl)sulfonylpropanamide
• CAS: 466671-23-8
• 化学式: C₂₄H₂₆N₂O₃S
• 分子量: 422.548
• InChiKey: RXDMXHINCNXFJA-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(N,N-dibenzylamino)-3-(p-tolylsulfonyl)propanamide 在 disodium hydrogenphosphate 、 sodium amalgam 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以91.5%的产率得到(S)-2-(N,N-dibenzylamino)propanamide
  参考文献：
  名称：

  Stereoselective cyanosilylation of α-sulfinylketimines or its covalently stabilized enamine tautomers. Synthesis of enantiomerically pure α-sulfinylmethyl-α-amino nitriles

  摘要：

  alpha-Sulfinylketimmes and beta-sulfinylenamines undergo reaction with delivery cyanide reagents such as TMSCN or TBDMSCN in the presence of either stoichiometric excesses of ZnCl2 or ZnBr2, or catalytic amount of Yb(TfO)(3). The use of ZnCl2 in alcohol solvents provides the best diastercoselectivity. It is mediated by a chelated transition state, the p-tolyl group driving the anti attack of the reagent. By using Yb(TfO)(3) poor diastereoselectivities but good yields are obtained. It seems that an iminium derivative originated by metal coordination with either the nitrogen or oxygen atom in the substrate is responsible for the observed results. Interestingly, beta-sulfinylenamines provide analogous a-amino nitriles in the same reaction conditions. It allowed the cyanosilylation of the covalently stabilized enamines arising from unstable beta-sulfinyl aldehydes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00234-x
• 作为产物：
  描述：

  (R)-(E)-N,N-dibenzyl-[2-(p-tolylsulfinyl)vinyl]amine 在 双氧水 、 potassium carbonate 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.75h， 生成 (R)-2-(N,N-dibenzylamino)-3-(p-tolylsulfonyl)propanamide
  参考文献：
  名称：

  Stereoselective cyanosilylation of α-sulfinylketimines or its covalently stabilized enamine tautomers. Synthesis of enantiomerically pure α-sulfinylmethyl-α-amino nitriles

  摘要：

  alpha-Sulfinylketimmes and beta-sulfinylenamines undergo reaction with delivery cyanide reagents such as TMSCN or TBDMSCN in the presence of either stoichiometric excesses of ZnCl2 or ZnBr2, or catalytic amount of Yb(TfO)(3). The use of ZnCl2 in alcohol solvents provides the best diastercoselectivity. It is mediated by a chelated transition state, the p-tolyl group driving the anti attack of the reagent. By using Yb(TfO)(3) poor diastereoselectivities but good yields are obtained. It seems that an iminium derivative originated by metal coordination with either the nitrogen or oxygen atom in the substrate is responsible for the observed results. Interestingly, beta-sulfinylenamines provide analogous a-amino nitriles in the same reaction conditions. It allowed the cyanosilylation of the covalently stabilized enamines arising from unstable beta-sulfinyl aldehydes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00234-x

文献信息

• Stereoselective cyanosilylation of α-sulfinylketimines or its covalently stabilized enamine tautomers. Synthesis of enantiomerically pure α-sulfinylmethyl-α-amino nitriles
  作者：Hassan Acherki、Carlos Alvarez-Ibarra、Alfonso-de-Dios、Maria L Quiroga

  DOI：10.1016/s0040-4020(02)00234-x

  日期：2002.4

  alpha-Sulfinylketimmes and beta-sulfinylenamines undergo reaction with delivery cyanide reagents such as TMSCN or TBDMSCN in the presence of either stoichiometric excesses of ZnCl2 or ZnBr2, or catalytic amount of Yb(TfO)(3). The use of ZnCl2 in alcohol solvents provides the best diastercoselectivity. It is mediated by a chelated transition state, the p-tolyl group driving the anti attack of the reagent. By using Yb(TfO)(3) poor diastereoselectivities but good yields are obtained. It seems that an iminium derivative originated by metal coordination with either the nitrogen or oxygen atom in the substrate is responsible for the observed results. Interestingly, beta-sulfinylenamines provide analogous a-amino nitriles in the same reaction conditions. It allowed the cyanosilylation of the covalently stabilized enamines arising from unstable beta-sulfinyl aldehydes. (C) 2002 Elsevier Science Ltd. All rights reserved.