(2S)-6-amino-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-(2,2,2-trifluoroacetyl)amino]hexanoic acid | 130414-30-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 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: (2S)-6-amino-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-(2,2,2-trifluoroacetyl)amino]hexanoic acid
• CAS: 130414-30-1
• 化学式: C₂₀H₂₇F₃N₂O₅
• 分子量: 432.4
• InChiKey: QKGKAQLXEOARHX-HOTGVXAUSA-N

物化性质

• 熔点：
  133-138 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

文献信息

• [EN] PROCESS FOR THE PRODUCTION OF LISINOPRIL<br/>[FR] PROCEDE DE PRODUCTION DE LISINOPRIL
  申请人：EOS ECZACIBASI OZGUN KIMYASAL

  公开号：WO2004000874A1

  公开（公告）日：2003-12-31

  The present invention provides a process for preparing N2-[1(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine and lisinopril thereof. Lisinopril shows excellent angiotensin converting enzyme inhibitor activity. Friedel-Crafts acylation of benzene with maleic anhydride in the presence of AlCl¿3? affords trans-β-benzoylacrylic acid. Treatment of benzoylacrylic acid with HCl gas in ethanol gives ethyl 2-chloro-4-oxo-4-phenylbutyrate in high yield. The coupling reaction between ethyl 2-chloro-4-oxo-4-phenylbutyrate and trifluoroacetyl-L-lysine benzyl ester in the presence of a base pair and sodium iodide produces alkyl lydine derivative with a good diastereoselectivity. Catalytic hydrogenation of lysine derivative with palladium gives N?2¿-[1(S)-ethoxycarbonyl-3-phenylpropyl]-N6-trifluoroacetyl-L-lysine. This intermediate is activated to form cyclic N-anhydride by using N,N-carbonyldiimidazole and coupled with L-proline methyl ester hydrochloride to give fully protected lisinopril derivative, which is converted into crude lisinopril by hydrolysis.

  本发明提供了一种制备N2-[1(S)-乙氧羰基-3-苯基丙基]-N6-三氟乙酰-L-赖氨酸及其琥珀酸二乙酯盐（Lisinopril）的方法。Lisinopril表现出优异的血管紧张素转换酶抑制活性。在AlCl3存在下，苯与马来酸酐进行Friedel-Crafts酰化反应，得到反式-β-苯甲酰丙烯酸。将苯甲酰丙烯酸与HCl气体在乙醇中处理，高收率得到乙酸2-氯-4-氧代-4-苯基丁酯。在碱对和碘化钠存在下，乙酸2-氯-4-氧代-4-苯基丁酯与三氟乙酰-L-赖氨酸苄酯进行偶联反应，产生具有良好对映选择性的烷基赖氨酸衍生物。使用钯进行催化氢化，得到N2-[1(S)-乙氧羰基-3-苯基丙基]-N6-三氟乙酰-L-赖氨酸。使用N,N-羰基二咪唑激活该中间体形成环状N-酐，并与L-脯氨酸甲酯盐偶联，形成完全保护的Lisinopril衍生物，通过水解转化为粗Lisinopril。
• PROCESS FOR THE PRODUCTION OF LISINOPRIL
  申请人：EOS Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ti Caret A.S.

  公开号：EP1513868A1

  公开（公告）日：2005-03-16
• STABILIZED MINIMAL COILED-COIL MIMETICS
  申请人：New York University

  公开号：EP3303367A1

  公开（公告）日：2018-04-11
• [EN] EFFECTIVE HAIR STYLING COMPOSITIONS AND PROCESSES<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE COIFFURE EFFICACES
  申请人：NUTECH VENTURES

  公开号：WO2016161360A1

  公开（公告）日：2016-10-06

  Morphology of hair is mainly determined by distribution of two types of cells 10 with different hydrophilicity. For both cells, hard a-keratin molecules (intermediate filaments, IFs) are the basic building units embedded in matrix proteins. The relatively hydrophilic cells contain less disulfide crosslinking and IFs mainly in helical conformation, while the relatively hydrophobic cells contain higher contents of disulfide bonds and IFs in both helix and parallel arrangements (see, e.g., Bryson et al., Journal of 15 Structural Biology, 2009, 166, 46). Hair styling compositions and processes are shown, more particularly compositions for disentangling or crosslinking hair that are useful in hair styling processes.
• [EN] STABILIZED MINIMAL COILED-COIL MIMETICS<br/>[FR] MIMÉTIQUES DE SUPERENROULEMENT MINIMAL STABILISÉS
  申请人：UNIV NEW YORK

  公开号：WO2016201007A1

  公开（公告）日：2016-12-15

  This invention relates to a macrostructure that includes an antiparallel coiled-coil structure shown below or a parallel coiled-coil structure shown below and described in the present application.