E-Ethyl-α-formamid-β-phenylacrylat | 40078-37-3

• 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: E-Ethyl-α-formamid-β-phenylacrylat
• 英文别名: Z-Ethyl-α-formamid-β-phenylacrylat；ethyl (E)-2-formamido-3-phenylprop-2-enoate
• CAS: 40078-37-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: NSIFWGFNWXAKOX-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-acetoxy-2-acetylamino-3-phenyl-propionic acid ethyl ester 在 三氟化硼乙醚 、 烯丙基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到ethyl 2-(acetylamino)-2-benzyl-4-pentenoate
  参考文献：
  名称：

  Synthesis of .alpha.-substituted .alpha.-amino acids via cationic intermediates

  摘要：

  A novel synthetic approach to racemic alpha-substituted alpha-amino acids is described. The key intermediates of this methodology are highly electrophilic iminium ions, bearing carbonyl substituents at both the iminium carbon and nitrogen atom. The preparation of precursors 8, 10a-c, and 12 includes electrochemical oxidation techniques according to literature procedures. When an alpha-methyl precursor (8 or 10a) was used, reactions with allylsilanes and silyl enol ethers led to the desired products, but elimination to dehydroalanine derivatives appeared to be an important side reaction. A major improvement in the yields of the desired products could be effected by using longer reaction times. In this way, efficient syntheses of protected alpha-methyl-alpha-amino acids could be developed. The elimination process appeared to be a more serious problem in the alpha-benzyl (10b) and alpha-allyl (10c) cases. On the other hand, the alpha-phenyl precursor 12 appeared to be highly useful, because the elimination is impossible in this case. High yields of alpha-phenyl-alpha-amino acid derivatives were obtained upon reaction of 12 with silicon-activated pi-nucleophiles. Deprotection led to various types of free alpha-substituted alpha-amino acids.

  DOI：

  10.1021/jo00064a011

文献信息

• Substituted imidazole compound and use thereof
  申请人：Kuroita Takanobu

  公开号：US20090227560A1

  公开（公告）日：2009-09-10

  The present invention relates to a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.

  本发明涉及一种由以下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。本发明的化合物具有优越的肾素抑制活性，因此可用作预防或治疗高血压、由高血压引起的各种器官损伤等的药物。
• Cyclic Amine Compound and Use Thereof for the Prophylaxis or Treatment of Hypertension
  申请人：Kuroita Takanobu

  公开号：US20100121048A1

  公开（公告）日：2010-05-13

  The present invention relates to a compound represented by the formula: (I) wherein ring A is a 5- or 6-membered aromatic heterocycle optionally having substituent (s); U, V and W are each independently C or N, provided that when any one of U, V and W is N, then the others should be C; Ra and Rb are each independently a cyclic group optionally having substituent(s), a C 1-10 alkyl group optionally having substituent(s), a C 2-10 alkenyl group optionally having substituent(s), or a C 2-10 alkynyl group optionally having substituent(s); X is a bond, or a spacer having 1 to 6 atoms in the main chain; Y is a spacer having 1 to 6 atoms in the main chain; Rc is a hydrocarbon group optionally containing heteroatom(s) as the constituting atom(s), which optionally has substituent(s); m and n are each independently 1 or 2; and ring B optionally further has substituent(s), or a salt thereof. The compound of the present invention has excellent renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.

  本发明涉及一种由式(I)表示的化合物：其中，环A是一种5或6成员的芳香杂环，可选地具有取代基；U、V和W分别独立地为C或N，但当U、V和W中的任何一个为N时，其他的应为C；Ra和Rb分别独立地为一个环状基团，可选地具有取代基；一个C1-10烷基，可选地具有取代基；一个C2-10烯基，可选地具有取代基；或一个C2-10炔基，可选地具有取代基；X是一条键或具有1到6个原子的主链间隔；Y是具有1到6个原子的主链间隔；Rc是一个含有杂原子作为构成原子的碳氢基团，可选地具有取代基；m和n分别独立地为1或2；环B可选地具有取代基，或其盐。本发明的化合物具有优异的肾素抑制活性，因此可用作预防或治疗高血压、高血压引起的各种器官损伤等的药物。
• [EN] CYCLIC AMINE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ AMINE CYCLIQUE ET UTILISATION DE CELUI-CI
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2007094513A2

  公开（公告）日：2007-08-23

  [EN] The present invention relates to a compound represented by the formula:( I ) wherein ring A is a 5- or 6-membered aromatic heterocycle optionally having substituent (s); U, V and W are each independently C or N, provided that when any one of U, V and W is N, then the others should be C; Ra and Rb are each independently a cyclic group optionally having substituent (s), a C_1-10 alkyl group optionally having substituent (s), a C_2-10 alkenyl group optionally having substituent (s), or a C_2-10alkynyl group optionally having substituent (s); X is a bond, or a spacer having 1 to 6 atoms in the main chain; Y is a spacer having 1 to 6 atoms in the main chain; Rc is a hydrocarbon group optionally containing heteroatom(s) as the constituting atom(s), which optionally has substituent (s); m and n are each independently 1 or 2; and ring B optionally further has substituent (s), or a salt thereof. The compound of the present invention has excellent renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension, and the like.
  [FR] La présente invention concerne un composé ou un sel de celui-ci représenté par la formule (I). Dans cette formule le cycle A est un hétérocycle aromatique ramifié à 5 ou 6 chaînons possédant éventuellement un ou plusieurs substituants, U, V et W sont chacun indépendamment C ou N, sous réserve que lorsque U, V ou W est N, les autres doivent être C, Ra et Rb sont chacun indépendamment un groupe cyclique possédant éventuellement un ou plusieurs substituants, un groupe alkyle en C_1-10 possédant éventuellement un ou plusieurs substituants, un groupe alkényle en C_2-10possédant éventuellement un ou plusieurs substituants, ou un groupe alkynile en C_2-10 possédant éventuellement un ou plusieurs substituants, X est une liaison ou un séparateur possédant 1 à 6 atomes dans la chaîne principale, Y est un séparateur possédant 1 à 6 atomes dans la chaîne principale, Rc est un groupe hydrocarbure contenant éventuellement un ou plusieurs hétéroatomes comme atomes constituants, qui possède éventuellement un ou plusieurs substituants, m et n sont chacun indépendamment 1 ou 2 et, le cycle B possède aussi éventuellement un ou plusieurs substituants. Le composé de cette invention possède une excellente activité inhibitrice de rénine, et convient donc comme agent pour la prophylaxie ou le traitement de l'hypertension, de divers dégradations d'organe imputables à l'hypertension et similaire.
• Synthesis of .alpha.-substituted .alpha.-amino acids via cationic intermediates
  作者：Eric C. Roos、M. Carmen Lopez、Michael A. Brook、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00064a011

  日期：1993.6

  A novel synthetic approach to racemic alpha-substituted alpha-amino acids is described. The key intermediates of this methodology are highly electrophilic iminium ions, bearing carbonyl substituents at both the iminium carbon and nitrogen atom. The preparation of precursors 8, 10a-c, and 12 includes electrochemical oxidation techniques according to literature procedures. When an alpha-methyl precursor (8 or 10a) was used, reactions with allylsilanes and silyl enol ethers led to the desired products, but elimination to dehydroalanine derivatives appeared to be an important side reaction. A major improvement in the yields of the desired products could be effected by using longer reaction times. In this way, efficient syntheses of protected alpha-methyl-alpha-amino acids could be developed. The elimination process appeared to be a more serious problem in the alpha-benzyl (10b) and alpha-allyl (10c) cases. On the other hand, the alpha-phenyl precursor 12 appeared to be highly useful, because the elimination is impossible in this case. High yields of alpha-phenyl-alpha-amino acid derivatives were obtained upon reaction of 12 with silicon-activated pi-nucleophiles. Deprotection led to various types of free alpha-substituted alpha-amino acids.