2-phenyl-2-(4'-toluenesulfonylamino)propionic acid methyl ester | 909731-90-4

• 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: 2-phenyl-2-(4'-toluenesulfonylamino)propionic acid methyl ester
• 英文别名: Methyl 2-[(4-methylphenyl)sulfonylamino]-2-phenylpropanoate；methyl 2-[(4-methylphenyl)sulfonylamino]-2-phenylpropanoate
• CAS: 909731-90-4
• 化学式: C₁₇H₁₉NO₄S
• 分子量: 333.408
• InChiKey: LOFQBBDMZSYCBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-(4'-toluenesulfonylamino)propionic acid methyl ester 在 氢溴酸 、 溶剂黄146 、 苯酚 作用下， 以88%的产率得到DL-2-氨基-2-苯基丙酸
  参考文献：
  名称：

  Sulfamidation of 2-Arylaldehydes and Ketones with Chloramine-T

  摘要：

  A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either alpha-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to alpha, alpha-disubstituted amino acids.

  DOI：

  10.1021/ol061410g
• 作为产物：
  描述：

  (+)-2-phenyl-2-(tolyl-4-sulfonylamino)propionaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 甲醇 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 12.08h， 生成 2-phenyl-2-(4'-toluenesulfonylamino)propionic acid methyl ester
  参考文献：
  名称：

  Sulfamidation of 2-Arylaldehydes and Ketones with Chloramine-T

  摘要：

  A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either alpha-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to alpha, alpha-disubstituted amino acids.

  DOI：

  10.1021/ol061410g

文献信息

• Sulfamidation of 2-Arylaldehydes and Ketones with Chloramine-T
  作者：Thomas Baumann、Michael Bächle、Stefan Bräse

  DOI：10.1021/ol061410g

  日期：2006.8.1

  A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either alpha-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to alpha, alpha-disubstituted amino acids.
• Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives
  作者：Caroline E. Hartmann、Thomas Baumann、Michael Bächle、Stefan Bräse

  DOI：10.1016/j.tetasy.2010.04.026

  日期：2010.6

  We herein present organocatalytic approaches to synthesize fluorinated and deuterated alpha-substituted phenylglycine derivatives. Whereas the addition of diethyl azodicarboxylate to fluorinated alpha-substituted aldehydes furnishes chiral non-racemic compounds, the use of chloramine-T as a nitrogen source represents a rapid access to sulfamidated fluorinated amino acid precursors. Additionally, further functionalization was achieved through the palladium-catalyzed coupling of a p-bromosubstituted aldehyde with a range of fluorine or deuterium-containing boronic acids. Oxidation of the aldehyde function and cleavage of the protection group of the nitrogen give way to the free fluorinated unnatural amino acids. (C) 2010 Elsevier Ltd. All rights reserved.