methyl 2-diazo-3-(m-trifluoromethyl)phenyl-3-[(N-tosyl)amino]propanoate

• 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: methyl 2-diazo-3-(m-trifluoromethyl)phenyl-3-[(N-tosyl)amino]propanoate
• 化学式: C₁₈H₁₆F₃N₃O₄S
• 分子量: 427.404
• InChiKey: ZCUBNOGLAMASNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  重氮乙酸甲酯 、 4-methyl-N-(3-(trifluoromethyl)benzylidene)benzenesulfonamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以51%的产率得到methyl 2-diazo-3-(m-trifluoromethyl)phenyl-3-[(N-tosyl)amino]propanoate
  参考文献：
  名称：

  Concise and diastereoselective approach to syn- and anti-N-tosyl-α-hydroxy β-amino acid derivatives

  摘要：

  The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy P-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give beta-(N-tosyl)amino alpha-diazoesters, followed by oxidation with Oxoneo to generate alpha-oxo esters, which were reduced with NaBH4 to yield the anti-N-losyl-alpha-hydroxy beta-amino ester, or hydrogenated with Pd/C (10%) as the catalyst to yield corresponding syn isomer, both in high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.054

文献信息

• Concise and diastereoselective approach to syn- and anti-N-tosyl-α-hydroxy β-amino acid derivatives
  作者：Yonghua Zhao、Nan Jiang、Shufeng Chen、Cheng Peng、Xiaomei Zhang、Yaping Zou、Shiwei Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2005.04.054

  日期：2005.7

  The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy P-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give beta-(N-tosyl)amino alpha-diazoesters, followed by oxidation with Oxoneo to generate alpha-oxo esters, which were reduced with NaBH4 to yield the anti-N-losyl-alpha-hydroxy beta-amino ester, or hydrogenated with Pd/C (10%) as the catalyst to yield corresponding syn isomer, both in high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.