(S)-tert-butyl 2-(diphenylmethyleneamino)-3-(perfluorophenyl)propanoate | 1207604-26-9

• 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: (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(perfluorophenyl)propanoate
• CAS: 1207604-26-9
• 化学式: C₂₆H₂₂F₅NO₂
• 分子量: 475.458
• InChiKey: AUQRHHRZXBVMOU-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(perfluorophenyl)propanoate 在 水 、 柠檬酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以91%的产率得到(S)-tert-butyl 2-amino-3-(perfluorophenyl)propanoate
  参考文献：
  名称：

  Incorporation of Fluorinated Phenylalanine Generates Highly Specific Inhibitor of Proteasome’s Chymotrypsin-like Sites

  摘要：

  Proteasomal processing is conducted by three individual catalytic subunits, namely beta 1, beta 2, and beta 5. Subunit-specific inhibitors are useful tools In dissecting the role of these individual Subunits and are leads toward the development of antitumor agents. We here report that the presence of fluorinated phenyl-alanine derivatives in peptide based proteasome inhibitors has a profound effect on inhibitor potency and selectivity, Specifically, compound 4a emerges as one of the most beta 5 specific inhibitors known to date.

  DOI：

  10.1021/jm9015685
• 作为产物：
  描述：

  N-二苯亚甲基-甘氨酸叔丁酯 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 2,7-bis[9-O-allylhydrocinchonidinium-N-methyl]naphthalene dibromide 、 potassium hydroxide 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 84.0h， 以100%的产率得到(S)-tert-butyl 2-(diphenylmethyleneamino)-3-(perfluorophenyl)propanoate
  参考文献：
  名称：

  Incorporation of Fluorinated Phenylalanine Generates Highly Specific Inhibitor of Proteasome’s Chymotrypsin-like Sites

  摘要：

  Proteasomal processing is conducted by three individual catalytic subunits, namely beta 1, beta 2, and beta 5. Subunit-specific inhibitors are useful tools In dissecting the role of these individual Subunits and are leads toward the development of antitumor agents. We here report that the presence of fluorinated phenyl-alanine derivatives in peptide based proteasome inhibitors has a profound effect on inhibitor potency and selectivity, Specifically, compound 4a emerges as one of the most beta 5 specific inhibitors known to date.

  DOI：

  10.1021/jm9015685

文献信息

• Enantioselective synthesis of fluorinated aromatic amino acids catalyzed by SPINOL-derived chiral quaternary ammonium salts†
  作者：Meng-Yu Rong、Jing Nie、Shen Li、Jun-An Ma

  DOI：10.1016/j.mcat.2023.113679

  日期：2024.1

  We report the synthesis of a new class of chiral quaternary ammonium salts featuring a rigid spirobiindane scaffold. These chiral quaternary ammonium salts were employed as catalysts in the phase-transfer catalytic asymmetric alkylation of tert‑butyl glycinate–benzophenone Schiff base with both fluorinated and non-fluorinated benzyl bromides. Under the established reaction conditions, a series of chiral

  我们报道了一种新型手性季铵盐的合成，该季铵盐具有刚性螺二茚满支架。这些手性季铵盐被用作甘氨酸叔丁酯-二苯甲酮席夫碱与氟化和非氟化苄基溴的相转移催化不对称烷基化反应的催化剂。在既定的反应条件下，以高产率和对映选择性获得了一系列手性氟化芳香族α-氨基酸衍生物，其中一些是具有生物学意义的化合物的关键中间体。