3-[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allylamino]-propionic acid methyl ester | 300363-42-2

• 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: 3-[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allylamino]-propionic acid methyl ester
• 英文别名: methyl 3-[[(2R)-1-[tert-butyl(diphenyl)silyl]oxybut-3-en-2-yl]amino]propanoate
• CAS: 300363-42-2
• 化学式: C₂₄H₃₃NO₃Si
• 分子量: 411.616
• InChiKey: LHGFTSXXXTYGEQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allylamino]-propionic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 3-[[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid
  参考文献：
  名称：

  Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N -allyl-β- N -keteniminium salts derived from ( R )-vinylglycinol

  摘要：

  A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00237-8
• 作为产物：
  描述：

  tert-butyl (R)-{1-[(tert-butyldiphenylsilyl)oxy]but-3-en-2-yl}carbamate 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allylamino]-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N -allyl-β- N -keteniminium salts derived from ( R )-vinylglycinol

  摘要：

  A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00237-8

文献信息

• Stereoselective synthesis of 2-substituted 3-azabicyclo[3.2.0]heptan-2-ones by [2+2]-cycloaddition of N -allyl-β- N -keteniminium salts derived from ( R )-vinylglycinol
  作者：Giuliano Delle Monache、Domenico Misiti、Patrizia Salvatore、Giovanni Zappia、Marco Pierini

  DOI：10.1016/s0957-4166(00)00237-8

  日期：2000.7

  A stereoselective synthesis of (1R,2R,5S)-2-benzyloxymethyl-3-azabicyclo[3.2.0]heptane-2-one was achieved, by intramolecular [2+2]-cycloaddition of (R)-vinylglycinol-derived N-allyl-beta-N-keteniminium salts, with high facial diastereoselection. The regio- and stereochemical courses have been qualitatively investigated by Molecular Mechanics calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.