ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate | 152359-60-9

• 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: ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate
• 英文别名: ethyl (5S,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-6-phenylhex-2-enoate；ethyl (E,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-6-phenylhex-2-enoate
• CAS: 152359-60-9
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: TXVFVOPTTHEDEM-RUMSDORHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid ethyl ester 、 (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids

  摘要：

  通过两条不同的途径，制备了四个对映异构体(2R或2S,5R或5S)-3-苄基-5-{(1S)-[(叔丁氧羰基)氨基]-2-苯乙基}四氢呋喃-2-酮(11、12、17和18)。由于呋喃酮是由(S)-苯丙氨酸衍生而来的，所有手性碳原子的绝对构型可以从它们的1H NMR谱中推断出来。这些呋喃酮容易水解成四个(2R或2S,4R或4S,5S)-2-苄基-5-[(叔丁氧羰基)氨基]-4-羟基-6-苯基丁酸(20-23)，是Phe-Phe肽键的羟基乙烯同分异构体。

  DOI：

  10.1135/cccc19980231
• 作为产物：
  描述：

  N-叔丁氧羰基-L-苯丙氨酸甲酯 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 ethyl (E)-(5S)-6-phenyl-5-[(tert-butyloxycarbonyl)amino]-4-oxo-2-hexenoate
  参考文献：
  名称：

  Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors

  摘要：

  Novel analogues of the angiotensin I-converting enzyme (ACE) inhibitor keto-ACE were synthesized via a facile Horner-Emmons olefination of a phosphonoketone precursor with ethyl glyoxylate. Introduction of a bulky aromatic tryptophan at the P'(2) position of keto-ACE resulted in a significant increase in C-domain-selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.003

文献信息

• Rhodium-catalysed redox isomerization of hydroxy alkynes to trans keto and hydroxy vinyl esters. A short and stereoselective synthesis of dipeptide isosters
  作者：M.K. Eddine Saïah、Roberto Pellicciari

  DOI：10.1016/0040-4039(95)00768-8

  日期：1995.6

  Tris(triphenylphosphine)Rhodium(I) Chloride in the presence trialkyl phosphine catalyses the isomerization of hydroxy alkynes to unsaturated trans keto and hydroxy esters depending on the nature of the phosphine. Dipeptide isosters were obtained in a an efficient manner by the application of this methodology.

  在三烷基膦存在下，三（三苯基膦）铑（I）氯化物取决于膦的性质，催化羟基炔烃异构化为不饱和的反式酮和羟基酯。通过使用该方法以有效的方式获得了二肽等排物。
• Angiotensin I-converting enzyme (ace) inhibitors
  申请人：Sturrock Edward

  公开号：US20090281160A1

  公开（公告）日：2009-11-12

  This invention relates to a process for the synthesis of ketomethylene derivatives of the tripeptide Phe-Gly-Pro (“keto-ACE”, compound 5 a ) and analogues thereof. The synthesis process proceeds via an α,β-unsaturated keto intermediate. A key feature of the process involves a Horner-Emmons olefination of the, -unsaturated keto-phosphonate with ethyl glyoxylate. Keto-ACE analogues produced by the process of the invention display C-domain selectivity.

  这项发明涉及一种合成三肽Phe-Gly-Pro的酮甲基衍生物（“酮-ACE”，化合物5a）及其类似物的过程。合成过程通过α，β-不饱和酮中间体进行。该过程的关键特征涉及将α，β-不饱和酮膦酸酯与乙酸乙酯进行Horner-Emmons烯化反应。根据本发明的过程生产的酮-ACE类似物表现出C-结构域选择性。
• Oxidation of α-diazoketones derived from<scp>L</scp>-amino acids and dipeptides using dimethyldioxirane. Synthesis and reactions of homochiral N-protected α-amino glyoxals
  作者：Paul Darkins、Noreen McCarthy、M. Anthony McKervey、Tao Ye

  DOI：10.1039/c39930001222

  日期：——

  Homochiral N-protected α-amino glyoxals are readily accessible by oxidation of α-diazoketones derived from natural amino acids and dipeptides using dimethyldioxirane in acetone; the glyoxals can be trapped efficiently in reactions such as Wittig olefination and condensation with amines and vicinal diamines.

  在丙酮中使用二甲基二氧环己烷氧化从天然氨基酸和二肽中提取的δ±-二氮酮，很容易获得同手性 N 保护的δ±-氨基乙二醛；乙二醛可以在诸如维蒂希油化反应以及与胺和邻位二胺的缩合反应中被有效地捕获。
• PEPTIDE COMPOUND AND APPLICATION THEREOF, AND COMPOSITION CONTAINING PEPTIDE COMPOUND
  申请人：XDCExplorer (Shanghai) Co., Ltd.

  公开号：EP3650464A1

  公开（公告）日：2020-05-13

  Disclosed are a peptide compound and an application thereof, and a composition containing the peptide compound. The present invention provides a peptide compound represented by formula (1), and a pharmaceutically acceptable salt, a tautomer, a solvate, a crystal form or a prodrug thereof. The compound has good stability and good activity for Kiss1R.         Cap-AA1-AA2-XX3-Asn-AA5-AA6-AA7-Leu-AA9-AA10-P     (1)

  本发明公开了一种多肽化合物及其应用，以及一种含有该多肽化合物的组合物。本发明提供了一种由式（1）表示的多肽化合物及其药学上可接受的盐、同系物、溶液、晶型或原药。该化合物对 Kiss1R 具有良好的稳定性和活性。 Cap-AA1-AA2-XX3-Asn-AA5-AA6-AA7-Leu-AA9-AA10-P (1)
• Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation
  作者：Kazuya Kobayashi、Tetsuo Narumi、Shinya Oishi、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1021/jo9005602

  日期：2009.6.19

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.