ethyl α-N-benzyloxycarbonyl-α,β-didehydroalaninate | 68185-02-4

• 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 α-N-benzyloxycarbonyl-α,β-didehydroalaninate
• 英文别名: Ethyl 2-(benzyloxycarbonylamino)acrylate；ethyl N-benzyloxycarbonyl-2-aminoacrylate；N-Carbobenzoxy-2,3-dihydroalaninaethylester；Aethyl-2-(benzyloxycarbonyl)aminoacrylat；Ethyl 2-{[(benzyloxy)carbonyl]amino}prop-2-enoate；ethyl 2-(phenylmethoxycarbonylamino)prop-2-enoate
• CAS: 68185-02-4
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: DVDCTYKWRDJBCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl α-N-benzyloxycarbonyl-α,β-didehydroalaninate 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 Aethyl-3-amino-2-(benzyloxycarbonyl)aminoacrylat
  参考文献：
  名称：

  轻松合成α，β-不饱和α，β-二氨基酸

  摘要：

  DOI：

  10.1016/s0040-4039(01)95271-2
• 作为产物：
  描述：

  N-Carbobenzoxy-2-acetoxyalaninaethylester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl α-N-benzyloxycarbonyl-α,β-didehydroalaninate
  参考文献：
  名称：

  Syntheses of amino acids and related compounds. 19. New versatile syntheses of 2-substituted-2-amino acid and 2,3-dehydro-2-amino acid derivatives

  摘要：

  DOI：

  10.1021/jo01317a017

文献信息

• Dehydrooligopeptides. I. The Facile Coupling of α-Amino Acids with α-Dehydroamino Acids to Dehydrodipeptides
  作者：Yasuchika Yonezawa、Chung-gi Shin、Yuji Ono、Juji Yoshimura

  DOI：10.1246/bcsj.53.2905

  日期：1980.10

  N-Cbz- or N-Tos-α-dehydroamino acid (DHA) and its ester were prepared by the condensation of 2-oxo carboxylic acid or ester with benzyl carbamate or p-toluenesulfonamide. Subsequently, the N-protected DHA and its N-free ester thus obtained were coupled with several L-α-amino acid esters and N-protected (Boc or Cbz)-L-α-amino acid respectively by the usual peptide synthetic methods to give a number

  N-Cbz-或N-Tos-α-脱氢氨基酸（DHA）及其酯是通过2-氧代羧酸或酯与氨基甲酸苄酯或对甲苯磺酰胺缩合制备的。随后，将由此获得的 N-保护的 DHA 及其无 N-酯分别与几种 L-α-氨基酸酯和 N-保护的（Boc 或 Cbz）-L-α-氨基酸通过通常的肽合成方法偶联到给出许多不同类型的脱氢二肽。获得的所有新 DHA 和脱氢二肽的构型均显示为 (Z)-几何。
• A New and Convenient Method for the Synthesis of Dehydroamino Acids Starting from Ethyl<b><i>N</i></b>-Boc- and<b><i>N</i></b>-<b><i>Z</i></b>-<b><i>α</i></b>-Tosylglycinates and Various Nitro Compounds
  作者：Tanemasa Nagano、Hideki Kinoshita

  DOI：10.1246/bcsj.73.1605

  日期：2000.7

  Ethyl N-Boc- and N-Z-α-tosylglycinates, which were readily available from t-butyl or benzyl carbamate, ethyl glyoxylate, and sodium p-toluenesulfinate in formic acid, were reacted with a variety of nitro compounds in the presence of a base to afford the corresponding α,β-didehydroamino acid derivatives in good yields. Eventually, it was found that the (Z)-isomer was predominantly formed in the present

  N-Boc- 和 NZ-α-甲苯磺酰基甘氨酸乙酯很容易从甲酸中的氨基甲酸叔丁酯或苄酯、乙醛酸乙酯和对甲苯亚磺酸钠中获得，在碱存在下与各种硝基化合物反应以良好的收率提供相应的α,β-二脱氢氨基酸衍生物。最终，发现在本方法中主要形成(Z)-异构体。
• Cesium (<i>Z</i>)-2-Carbomethoxyethenethiolate: A Reagent for the Preparation of (<i>Z</i>)-2-Carbomethoxyethenyl Thioethers Including Selected Cysteine and Homocysteine Derivatives
  作者：Jennifer S. O'Donnell、Suneel P. Singh、Thomas A. Metcalf、Adrian L. Schwan

  DOI：10.1002/ejoc.200801025

  日期：2009.2

  standard and sometimes troubling conjugate addition reaction of thiols to alkyl propiolates, a new reagent, cesium (Z)-2-carbomethoxyethenethiolate, is introduced. The cesium carbonate mediated methanolysis of (Z)-2-carbomethoxyethenyl thiolacetate at low temperature creates cesium (Z)-2-carbomethoxyethenethiolate in solution. For base-insensitive and solvolytically stable electrophiles, efficient substitution

  作为规避硫醇与丙炔酸烷基酯的标准且有时令人不安的共轭加成反应的一种手段，引入了一种新试剂，即 (Z)-2-碳甲氧基乙硫醇铯。碳酸铯介导的 (Z)-2- 碳甲氧基乙硫醚乙酸酯在低温下的甲醇分解产生溶液中的 (Z)-2-碳甲氧基乙硫醇铯。对于碱不敏感和溶剂分解稳定的亲电试剂，可以通过直接引入亲电试剂来实现有效的取代。条件适合于对碱敏感的半胱氨酸衍生物，并且使用 DMF 作为共溶剂允许以高对映体纯度 (>99:1 er) 和良好的 Z/E 分离 (Z)-2-碳甲氧基乙烯基半胱氨酸硫醚比率。没有碳取代反应的证据。(© Wiley-VCH Verlag GmbH & Co. KGaA,
• Process for the Preparation of 2-azabicyclo[3.3.0]octane-3-carboxylic Acid Derivatives
  申请人：Knaup Günter

  公开号：US20090306404A1

  公开（公告）日：2009-12-10

  The present invention is aimed at a process for the preparation of compounds of the general formula (I). The objective process is in this case based on the Michael reaction of compounds of the general formula (III) with compounds of the general formula (IV), with subsequent hydrogenation and cyclization of the intermediates of the formula (II) obtained.

  本发明旨在提供一种制备通式（I）化合物的过程。该过程的目标是基于通式（III）化合物与通式（IV）化合物的Michael反应，随后对所得到的中间体通式（II）进行氢化和环化。
• Process for the preparation of 2-azabicyclo[3.3.0]octane-3-carboxylic Acid Derivatives
  申请人：Evonik Degussa GmbH

  公开号：US07935831B2

  公开（公告）日：2011-05-03

  The present invention is aimed at a process for the preparation of compounds of the general formula (I). The objective process is in this case based on the Michael reaction of compounds of the general formula (III) with compounds of the general formula (IV), with subsequent hydrogenation and cyclization of the intermediates of the formula (II) obtained.

  本发明旨在提供一种制备通式（I）化合物的方法。该方法基于通式（III）化合物与通式（IV）化合物的Michael反应，随后对得到的中间体通式（II）进行加氢和环化处理。