ethyl N-benzyloxycarbonylphenylalaninate | 42998-44-7

• 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: ethyl N-benzyloxycarbonylphenylalaninate
• 英文别名: Ethyl N-(benzyloxycarbonyl)-D-phenylalaninate；rac-N-benzyloxycarbonyl-phenylalanine ethyl ester；N-Benzyloxycarbonyl-phenylalaninethylester；N-benzyloxycarbonyl-phenylalanine ethyl ester；N-Benzyloxycarbonyl-phenylalanin-aethylester；Ethyl 3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 42998-44-7
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: XLLUIEKQXIOPDX-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  489.0±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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 N-benzyloxycarbonylphenylalaninate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 N-Cbz-D-苯丙氨醛
  参考文献：
  名称：

  Misiti, Domenico; Zappia, Giovanni; Delle Monache, Giuliano Delle, Liebigs Annalen, 1996, # 2, p. 235 - 238

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-azido-3-phenylacrylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ethyl N-benzyloxycarbonylphenylalaninate
  参考文献：
  名称：

  Synthesis of Phenylalanine Analogs

  摘要：

  A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the alpha-azidocinnamate in moderate yield. Hydrogenation of alpha-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.

  DOI：

  10.1002/jccs.200500150

文献信息

• Amino Acids and Peptides. XII. Phosphorus in Organic Synthesis. VIII. Reaction of Malonic Acid Half Esters with Diphenyl Phosphorazidate
  作者：KUNIHIRO NINOMIYA、TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.22.1398

  日期：——

  Application of the modified Curtius reaction by DPPA to some malonic acid half esters revealed that esterification occurred in a one-step process but the rearrangement reaction took place in a two-in-one-reaction procedure, the results of which are summarized in Tables I and II. The latter procedure may provide a new simple method for the synthesis of α-amino acids.

  通过DPPA对一些丙二酸半酯进行改良的Curtius反应的应用发现，酯化过程是一步完成的，但重排反应是在一个二合一反应程序中进行的，其结果总结在表I和表II中。后一程序可能为α-氨基酸的合成提供了一种新的简单方法。
• Poststatin, a New Inhibitor of Prolyl Endopeptidase. V. Endopeptidase Inhibitory Activity of Poststatin Analogues.
  作者：MAKOTO TSUDA、YASUHIKO MURAOKA、MACHIKO NAGAI、TAKAAKI AOYAGI、TOMIO TAKEUCHI

  DOI：10.7164/antibiotics.49.890

  日期：——

  Thirty analogues of poststatin were synthesized, and their inhibitory activities against prolyl endopeptidase, human leukocyte elastase and cathepsin B were measured. The α-ketone was essential and the S configuration was preferable to the R configuration in the β-substituted-β-amino-α-oxopropionic acid moiety of poststatin analogues for endopeptidase inhibitory activity. The analogue in which the D-leucine residue of poststatin was replaced by L-leucine showed strong inhibitory activity to cathepsin B. Introduction of an aromatic group into the P4 position and proline into the P2 position increased inhibitory activity to elastase. Benzyloxycarbonyl-L-homophenylalanyl-(RS)-3-amino-2-oxovaleryl-D-leucyl-L-valine was about 6 times more active to prolyl endopeptidase than natural poststatin.

  合成了30个波杀菌蛋白类似物，并测定了它们对脯氨酰内肽酶、人白细胞弹性蛋白酶和组织蛋白酶B的抑制活性。对内肽酶抑制活性来说，α–酮基非常重要，β–取代–β–氨基–α–氧代丙酸部分的S构型比R构型更为优越。用L–亮氨酸代替波杀菌蛋白中的D–亮氨酸得到的类似物对组织蛋白酶B具有很强的抑制活性。将芳香基团引入到P4位和将脯氨酸引入到P2位使对弹性蛋白酶的抑制活性增强。苄氧羰基–L–高苯丙氨酰–(RS)–3–氨基–2–氧代戊二酰–D–亮氨酰–L–缬氨酸对脯氨酰内肽酶的活性约为天然波杀菌蛋白的6倍。
• PROCESS FOR THE PREPARATION OF ALPHA-CHLOROKETONES FROM ALKYL ESTERS
  申请人：Nugent Aloysius William

  公开号：US20050090670A1

  公开（公告）日：2005-04-28

  The present invention relates to a process for the preparation of α-chloroketones from readily available alkyl esters by the reaction of a sulfoxonium ylide on said alkyl esters to generate a keto sulfoxonium ylide that is in turn treated with anhydrous HCl.

  本发明涉及一种从易得的烷基酯通过磺醚锂化亚胺与该烷基酯发生反应制备α-氯酮的方法，生成一个酮基磺醚锂化亚胺，然后用无水HCl处理该酮基磺醚锂化亚胺。
• Approaches to the Synthesis of Cytochalasans. Part 3. Synthesis of a substituted tetrahydroisoindolinone moiety possessing the same relative configuration as proxiphomin
  作者：Tibur Schmidlin、Werner Züurcher、Christoph Tamm

  DOI：10.1002/hlca.19810640125

  日期：1981.2.4

  analysis of its O-acetyl derivative 16 [5]. Ring closure of the hydroxy acid 14 gave the lactone 17, corresponding to the natural product 1 as to the configuration. The presence of the N-benzyloxycarbonyl group in lactone 6 has been shown to be essential for the above-mentioned ‘inversion’ at C(9), because no configurational change occurred with the N-unprotected lactone 8 when treated under the same conditions

  描述了对应于脯氨酰胺（1）的四氢异吲哚满酮部分的总合成，其带有用于连接大环的官能团。外消旋2-（苄氧基羰基-氨基）-3-苯基丙醛（2）与（4-甲基-2,4-己二烯基）丙二酸甲酯（3）的Knoevenagel-Cope缩合产生（E）-和（Z）的混合物-烯烃4a和4b，其在加热时经历分子内Diels-Alder环化（参见方案1）。从所得产物中分离出四氢异吲哚啉衍生物6。X射线分析6 [5]揭示了在C（3），C（4），C（5）和C（8）上与1中相同的相对配置，但在C（9）处没有。用KOH水解6伴随着C（9）构型的变化，生成羟基酸14，该羟基酸14被转化为羟基酯11（参见方案4）。X射线分析O-乙酰基衍生物16 [5]证实了顺式-内酰胺环在11中的存在。羟基酸14的闭环得到内酯17，其对应于天然产物1关于配置。已经证明内酯6中N-苄氧基羰基的存在对于C（9）的上述“转化”是必不可少的，因为当在相同
• A novel process for the preparation of bestatin derivatives and intermediates thereof
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0156279A2

  公开（公告）日：1985-10-02

  The present invention relates to a new method of preparing bestatin derivatives of the formula wherein Ph is an optionally substituted phenyl group and Leu represents a leucine residue, and to an intermediate of the formula where Ph is as defined above.

  本发明涉及一种制备式中 Ph 为任选取代的苯基和 Leu 代表亮氨酸残基的贝他丁衍生物的新方法，以及式中 Ph 如上定义的中间体。

表征谱图