3-[[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid | 300363-44-4

• 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: 3-[[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid
• 英文别名: 3-[[(2R)-1-[tert-butyl(diphenyl)silyl]oxybut-3-en-2-yl]-(4-methylphenyl)sulfonylamino]propanoic acid
• CAS: 300363-44-4
• 化学式: C₃₀H₃₇NO₅SSi
• 分子量: 551.779
• InChiKey: UFRWBRYMZUEBDP-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-((R)-1-Benzyloxymethyl-allyl)-4-methyl-N-(3-oxo-3-pyrrolidin-1-yl-propyl)-benzenesulfonamide
  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：

  3-[[(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-allyl]-(toluene-4-sulfonyl)-amino]-propionic acid methyl ester 在 lithium hydroxide 作用下， 以 丙酮 为溶剂， 以86%的产率得到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

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.