(+/-)-trans-5-phenyl-4-amino-2-pentenoic acid ethyl ester

• 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: (+/-)-trans-5-phenyl-4-amino-2-pentenoic acid ethyl ester
• 英文别名: (e)-Ethyl 4-amino-5-phenylpent-2-enoate；ethyl (E)-4-amino-5-phenylpent-2-enoate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: OSOJJKZDZDPLSA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-5-phenyl-4-amino-2-pentenoic acid ethyl ester 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-trans-5-phenyl-4-[((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)amino]-2-pentenoic acid ethyl ester 、 (R)-trans-5-phenyl-4-[((R)-α-methoxy-α-(trifluoromethyl)phenylacetyl)amino]-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993
• 作为产物：
  描述：

  (+/-)-trans-5-phenyl-4-[(triisopropylsilyl)amino]-pent-2-enoic acid ethyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (+/-)-trans-5-phenyl-4-amino-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Enantiomerically Pure α-Amino Aldehydes from Silylated α-Amino Acids

  摘要：

  The disilylation of alpha-amino acids 1 to provide 2 (72-87%) was achieved without racemization. An unprecedented borane-mediated semi-reduction strategy was devised to convert 2 to stable, isolable oxazaborolidines 3 (100%) which were hydrolyzed to provide 5 (49-60%) as pure, stable compounds. Analysis of the Mosher amides (8) of the gamma-amino esters 7 reveals that <= 2% racemization occurs in the 1 -> 8 conversions.

  DOI：

  10.1021/ol7028993

文献信息

• [EN] NOVEL N-ACETYL-L-LEUCYL-L-LEUCYL-L-NORLEUCINAL (ALLN) DERIVATIVE COMPOUND, COMPOSITION FOR PREVENTING OR TREATING MALARIA, CONTAINING SAME AS ACTIVE INGREDIENT, AND USE THEREOF<br/>[FR] NOUVEAU COMPOSÉ DÉRIVÉ N-ACÉTYL-L-LEUCYL-L-LEUCYL-L-NORLEUCINAL (ALLN), COMPOSITION POUR LA PRÉVENTION OU LE TRAITEMENT DU PALUDISME, CONTENANT LEDIT COMPOSÉ UTILISÉ COMME PRINCIPE ACTIF, ET SON UTILISATION
  申请人：WONKWANG UNIV CT IND ACAD COOP

  公开号：WO2014084471A1

  公开（公告）日：2014-06-05

  본 발명은 ALLN 유도체 화합물을 유효성분으로 함유하는 항 말라리아 조성물에 관한 것으로, 본 발명의 화합물들은 ALLN (N-acetyl-L-Leucyl-Lleucyl-L-norleucinal) 유도체 화합물을 유효성분으로 함유하는 말라리아 감염 질환의 예방 및 치료용 약학조성물로 사용할 수 있다.