(+)-2-phenyl-2-(tolyl-4-sulfonylamino)propionaldehyde | 909731-75-5

• 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-(tolyl-4-sulfonylamino)propionaldehyde
• 英文别名: 2-phenyl-2-(4'-toluenesulfonylamino)propionaldehyde；4-methyl-N-(1-oxo-2-phenylpropan-2-yl)benzenesulfonamide
• CAS: 909731-75-5
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: OFNFBENLANAWNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-2-phenyl-2-(tolyl-4-sulfonylamino)propionaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 氢溴酸 、 双氧水 、 溶剂黄146 、 苯酚 作用下， 以 甲醇 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 12.08h， 生成 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-苯基丙醛 、 chloroamine-T 在 L-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以90%的产率得到(+)-2-phenyl-2-(tolyl-4-sulfonylamino)propionaldehyde
  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

• Direct Asymmetric α-Sulfamidation of α-Branched Aldehydes: A Novel Approach to Enamine Catalysis
  作者：Henning Vogt、Thomas Baumann、Martin Nieger、Stefan Bräse

  DOI：10.1002/ejoc.200600587

  日期：2006.12

  catalyst, aldehyde, sulfonyl chloride and sodium azide. The proposed mechanism differs fundamentally from the mechanistic model usually ascribed to enamine catalysis, containing as a key step the diastereoselective cycloaddition of the azide to an enamine formed in situ. The products obtained in the reaction can be converted into the corresponding unnatural amino acids in two additional steps.(© Wiley-VCH

  α-支化醛和磺酰叠氮化物之间的脯氨酸催化反应提供了比例结构稳定的 α-磺酰胺化产物，ee 值高达 86%。反应也可以用催化剂、醛、磺酰氯和叠氮化钠以一锅法进行。所提出的机制从根本上不同于通常归因于烯胺催化的机制模型，其中包含叠氮化物与原位形成的烯胺的非对映选择性环加成反应作为关键步骤。反应中获得的产物可以通过两个额外的步骤转化为相应的非天然氨基酸。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• 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.
• 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.