N-cyclohexyl-L-phenylalanine methyl ester | 66399-73-3

• 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: N-cyclohexyl-L-phenylalanine methyl ester
• 英文别名: methyl N-(cyclohexyl)phenylalaninate；α-(N-Cyclohexyl)amino-phenylpropionsaeuremethylester；N-Cyclohexyl-L-phenylalanine methyl ester；methyl (2S)-2-(cyclohexylamino)-3-phenylpropanoate
• CAS: 66399-73-3
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: ZJRMNAZXELIPQG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-L-phenylalanine methyl ester 、 甲基溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到N-cyclohexyl-1,1-dimethyl-L-phenylalaninol
  参考文献：
  名称：

  Sterically encumbered chiral amino alcohols for titanium-catalyzed asymmetric intramolecular hydroamination of aminoallenes

  摘要：

  A variety of sterically encumbered amino alcohol ligands were prepared in a two-step modular synthesis. The titanium complexes of these ligands were prepared in situ and used as catalysts for hydroamination. The intramolecular hydroamination of 6-methyl-hepta-4,5-dienylamine at 135 degrees C with 5 mol % catalyst gave exclusively 2-(2-methyl-propenyl)-pyrrolidine with enantiomeric excesses up to 16%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.013
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 苯酚 在 palladium 10% on activated carbon 、 sodium formate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 以64%的产率得到N-cyclohexyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

  摘要：

  Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cydohexylamines. This reaction works at rt for 12 h or at 60 degrees C under mictowave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexyl-amines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h(-1)).

  DOI：

  10.1021/acs.orglett.5b01842

文献信息

• Studies on the reduction and reductive alkylation of amino acid-derived spirocyclic 2,6-dioxopiperazines
  作者：Juan A. González-Vera、Pilar Ventosa-Andrés、Joanne Casey、M. Teresa García-López、Rosario Herranz

  DOI：10.1016/j.tet.2007.01.022

  日期：2007.3

  The regio- and diastereoselective reduction and reductive alkylation of 3-spiro-2,6-dioxopiperazines are described via a two-step process, which involves addition of NaBH4 or Grignard reagents, followed by TFA-mediated dehydration with a second NaBH4 addition. The results show that the reactivity of 2,6-dioxopiperazines is limited by their steric hindrance and by the volume of the nucleophile, which preferably add to the C-6 carbonylic carbon with complete diastereoselectivity. The diastereoselectivity of the first step is mainly governed by electronic factors, which direct the addition of the nucleophile from the most hindered face, while in the second step, the NaBH4 attacks from the less crowded face. This second step proceeds with partial or complete racemization. (c) 2007 Elsevier Ltd. All rights reserved.
• Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines
  作者：Varsha R. Jumde、Elena Petricci、Chiara Petrucci、Niccolò Santillo、Maurizio Taddei、Luigi Vaccaro

  DOI：10.1021/acs.orglett.5b01842

  日期：2015.8.21

  Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cydohexylamines. This reaction works at rt for 12 h or at 60 degrees C under mictowave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexyl-amines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h(-1)).
• Sterically encumbered chiral amino alcohols for titanium-catalyzed asymmetric intramolecular hydroamination of aminoallenes
  作者：Amanda J. Hickman、Lauren D. Hughs、Casey M. Jones、Hanhan Li、Joanne E. Redford、Samuel J. Sobelman、J. Andrew Kouzelos、Adam. R. Johnson

  DOI：10.1016/j.tetasy.2009.04.013

  日期：2009.6

  A variety of sterically encumbered amino alcohol ligands were prepared in a two-step modular synthesis. The titanium complexes of these ligands were prepared in situ and used as catalysts for hydroamination. The intramolecular hydroamination of 6-methyl-hepta-4,5-dienylamine at 135 degrees C with 5 mol % catalyst gave exclusively 2-(2-methyl-propenyl)-pyrrolidine with enantiomeric excesses up to 16%. (C) 2009 Elsevier Ltd. All rights reserved.