(3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester | 157683-55-1

• 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: (3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester
• 英文别名: methyl (3S)-2-oxo-4-phenyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 157683-55-1
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: KGYPRYDSKBINNA-INIZCTEOSA-N

物化性质

• 沸点：
  524.2±50.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 zinc(II) tetrahydroborate 、 氢溴酸 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氘代乙腈 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.83h， 生成 (3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester
  参考文献：
  名称：

  Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin

  摘要：

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00883-8
• 作为产物：
  描述：

  methyl (3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoate 在 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester
  参考文献：
  名称：

  Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

  摘要：

  Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00342-3

文献信息

• Synthesis of cyanoketophosphoranes, precursors of β-amino-α-keto-esters from UNCAs
  作者：Marielle Paris、Catherine Pothion、Christine Michalak、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(98)01504-4

  日期：1998.9

  Cyanomethylene triphenylphosphoranes of N-protected amino acids were synthesized from the corresponding N-urethane protected α-amino acid N-carboxyanhydrides (UNCAs) by reaction with cyanomethyltriphenylphosphonium chloride in good yields. These compounds are precursors of α-keto esters which are candidates for mimicking the tetrahedric transition state in enzyme inhibitors.

  由N-氨基甲酸酯保护的α-氨基酸N-羧基酸酐（UNCA）通过与氰基甲基三苯基chloride氯化物反应，以高收率合成了N-保护氨基酸的氰基亚甲基三苯基膦。这些化合物是α-酮酯的前体，它们是模拟酶抑制剂中四面体过渡态的候选物。
• PROCESS FOR REDUCING $G(a)-AMINO KETONES
  申请人：KANEKA CORPORATION

  公开号：EP0969000A1

  公开（公告）日：2000-01-05

  The present invention has its objects to provide a method for reducing α-aminoketone derivatives under mild conditions with high stereoselectivity. This invention is a method for reducing α-aminoketone which comprises reacting an α-aminoketone derivative of general formula (1) with a compound prepared from an organoaluminum compound of general formula (4), a sulfonic acid derivative of general formula (5), and an alcohol compound of general formula (6) to give an α-aminoalcohol derivative of general formula (7).

  本发明的目的是提供一种在温和条件下以高立体选择性还原α-氨基酮衍生物的方法。 本发明是一种还原α-氨基酮的方法，它包括将通式(1)的α-氨基酮衍生物与由通式(4)的有机铝化合物、通式(5)的磺酸衍生物和通式(6)的醇化合物制备的化合物反应，得到通式(7)的α-氨基醇衍生物。
• (Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides
  作者：Harry H. Wasserman、Wen-Bin Ho

  DOI：10.1021/jo00095a005

  日期：1994.8

  Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes. The resulting ylides may then be oxidatively cleaved with ozone to form alpha,beta-diketonitriles. These highly electrophilic products may then be converted in situ to alpha-keto acids, esters, and amides.
• First synthesis of enantiomerically pure N-protected β-amino-α-keto esters from α-amino acids and dipeptides
  作者：Paul Darkins、Noreen McCarthy、M. Anthony、McKervey、Kevin O'Donnell、Tao Ye、Brian Walker

  DOI：10.1016/s0957-4166(00)86171-6

  日期：1994.1

  A racemization-free route from N-protected alpha-amino acids and dipeptides to N-protected beta-amino-alpha-keto esters is described, involving the sequence: diazoketone formation. Wolff rearrangement in methanol, diazo transfer, and oxidation with dimethyldioxirane.
• Wasserman Harry H., Ho Wen-Bin, J. Org. Chem, 59 (1994) N 16, S 4364-4366
  作者：Wasserman Harry H., Ho Wen-Bin

  DOI：——

  日期：——