(S)-N-benzyl-5-[(tert-butoxycarbonyl)-amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanamide | 1408237-89-7

• 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: (S)-N-benzyl-5-[(tert-butoxycarbonyl)-amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanamide
• 英文别名: tert-butyl N-[(4S)-5-(benzylamino)-4-[[(1S)-1-cyano-2-phenylethyl]amino]-5-oxopentyl]carbamate
• CAS: 1408237-89-7
• 化学式: C₂₆H₃₄N₄O₃
• 分子量: 450.581
• InChiKey: IZCVDSZJNGLFCF-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyl-5-[(tert-butoxycarbonyl)-amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanamide 、 异氰酸苄酯 以 neat (no solvent) 为溶剂， 以93%的产率得到tert-butyl N-[(4S)-5-(benzylamino)-4-[benzylcarbamoyl-[(1S)-1-cyano-2-phenylethyl]amino]-5-oxopentyl]carbamate
  参考文献：
  名称：

  Solvent-Free Synthesis of α-Amino Nitrile-Derived Ureas

  摘要：

  An efficient and environmentally friendly methodology for the solvent-free synthesis of alpha-amino nitrile derived ureas from alpha-amino acid based amino nitriles has been developed. At room temperature no epimerization was observed in the resulting ureas, but under microwave heating, epimerization occurred at the chiral center bearing the cyano group.

  DOI：

  10.1021/ol303452r
• 作为产物：
  描述：

  (S)-methyl 5-[(tert-butoxycarbonyl)amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanoate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 (S)-N-benzyl-5-[(tert-butoxycarbonyl)-amino]-2-[((S)-1-cyano-2-phenylethyl)amino]-pentanamide
  参考文献：
  名称：

  A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

  摘要：

  Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.009

文献信息

• A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles
  作者：Pilar Ventosa-Andrés、M. Teresa García-López、Rosario Herranz

  DOI：10.1016/j.tetasy.2012.07.009

  日期：2012.8

  Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.
• Solvent-Free Synthesis of α-Amino Nitrile-Derived Ureas
  作者：Pilar Ventosa-Andrés、Juan A. González-Vera、M. Teresa García-López、Rosario Herranz

  DOI：10.1021/ol303452r

  日期：2013.2.1

  An efficient and environmentally friendly methodology for the solvent-free synthesis of alpha-amino nitrile derived ureas from alpha-amino acid based amino nitriles has been developed. At room temperature no epimerization was observed in the resulting ureas, but under microwave heating, epimerization occurred at the chiral center bearing the cyano group.