(+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionamide | 86900-31-4

• 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-phenyl-3-(toluene-4-sulfonylamino)-propionamide
• 英文别名: (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid amide；(+/-)-3-Phenyl-3-(toluol-4-sulfonylamino)-propionsaeure-amid；3-[(4-Methylphenyl)sulfonylamino]-3-phenylpropanamide；3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanamide
• CAS: 86900-31-4
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: REAQEMFWLXSLFU-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C
• 沸点：
  566.6±60.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-cyano-1-phenylethyl)-4-methylbenzenesulfonamide 在 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionamide
  参考文献：
  名称：

  Synthesis and microbial transformation of β-amino nitriles

  摘要：

  Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce beta-amino amides and acids from beta-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitrites gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.057

文献信息

• A new approach to β-amino acids: biotransformation of N-protected β-amino nitriles
  作者：Margit Preiml、Kerstin Hillmayer、Norbert Klempier

  DOI：10.1016/s0040-4039(03)01136-5

  日期：2003.6

  A number of novel N-protected β-amino nitriles were prepared as substrates for two nitrile-converting microorganisms, Rhodococcus sp. R312 and Rhodococcus erythropolis NCIMB 11540. The respective biotransformation products, β-amino acids, are known to be pharmacological very potent compounds.

  制备了许多新颖的N保护的β-氨基腈作为两种腈转化微生物Rhodococcus sp。的底物。R312和Rhodococcus erythropolis NCIMB11540。已知的各个生物转化产物β-氨基酸是药理学上非常有效的化合物。
• Synthesis and microbial transformation of β-amino nitriles
  作者：Margit Winkler、Ludmila Martínková、Astrid C. Knall、Stefan Krahulec、Norbert Klempier

  DOI：10.1016/j.tet.2005.02.057

  日期：2005.4

  Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce beta-amino amides and acids from beta-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitrites gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work. (c) 2005 Elsevier Ltd. All rights reserved.