(S)-3-phenyl-2-ureido-propionic acid | 949-45-1

• 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: (S)-3-phenyl-2-ureido-propionic acid
• 英文别名: N-carbamyl-L-phenylalanine；(S)-(+)-N-carbamoylphenylalanine；N-carbamoyl-L-phenylalanine；N-carbamoylphenylalanine；(2S)-2-(carbamoylamino)-3-phenylpropanoic acid
• CAS: 949-45-1
• 化学式: C₁₀H₁₂N₂O₃
• mdl: MFCD09863543
• 分子量: 208.217
• InChiKey: IPWQOZCSQLTKOI-QMMMGPOBSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  406.6±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)
• 溶解度：
  0.01 M

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-phenyl-2-ureido-propionic acid 在 氢氧化钾 、 sodium hypochlorite 、 肼 、 二乙胺 作用下， 以 盐酸 、 甲苯 、 乙醇 为溶剂， 反应 2.5h， 以75%的产率得到(S)-2-hydrazinyl-3-phenylpropanoic acid
  参考文献：
  名称：

  New pyrazole containing bicarboxylic α-amino acids: mimics of the cis amide bond

  摘要：

  A series of novel optically active oc-amino acids, containing a pyrazole ring, which can be regarded as building blocks for peptidomimetics, have been prepared starting from readily available oc-amino acids. The synthetic strategy employed allows the regio- and stereoselective preparation of 1,3- or 1,5-substituted pyrazolyl rings. The pyrazole containing peptidomimetics can be considered as analogues of peptides with a cis amide bond. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01847-x
• 作为产物：
  描述：

  L-苯丙氨酸盐酸盐 在 potassium cyanate 作用下， 以 水 为溶剂， 反应 4.0h， 以94%的产率得到(S)-3-phenyl-2-ureido-propionic acid
  参考文献：
  名称：

  Practical synthesis of optically active α-hydrazino acids from α-amino acids

  摘要：

  DOI：

  10.1016/s0040-4020(01)90026-2

文献信息

• Rapid and Efficient Microwave‐Assisted Synthesis of<i>N</i>‐Carbamoyl‐<scp>L</scp>‐amino Acids
  作者：Giancarlo Verardo、Paola Geatti、Paolo Strazzolini

  DOI：10.1080/00397910701317068

  日期：2007.6.1

  synthesis of N‐carbamoyl‐L‐amino acids is reported. The procedure, involving the reaction between urea and α‐amino acids sodium salts, was performed under microwave conditions using an unmodified domestic microwave oven. A careful study of the operative conditions indicated proline (1d) as the less reactive substrate and phenylglycine (1e) as the more reactive one among all the α‐amino acids tested. Substitution

  摘要 报道了一种快速有效的合成 N-氨基甲酰基-L-氨基酸的方法。该过程涉及尿素和 α-氨基酸钠盐之间的反应，在微波条件下使用未经改造的家用微波炉进行。对操作条件的仔细研究表明，脯氨酸 (1d) 是反应性较低的底物，而苯基甘氨酸 (1e) 是所有测试的 α-氨基酸中反应性较强的底物。用氰酸钾取代尿素产生相应的 N-氨基甲酰基衍生物的低转化率，并报告了对这一结果的可能解释。
• Investigation of<i>N</i>-carbamoylamino acid nitrosation by {NO + O₂} in the solid-gas phase. Effects of NO<i>x</i>speciation and kinetic evidence for a multiple-stage process
  作者：Olivier Lagrille、Jacques Taillades、Laurent Boiteau、Auguste Commeyras

  DOI：10.1002/poc.1164

  日期：2007.4

  Nitrosation of N-carbamoylamino acids (CAA) by gaseous NO + O2, an interesting synthetic pathway to amino acid N-carboxyanhydrides (NCA), alternative to the phosgene route, was investigated on N-carbamoyl-valine either in acetonitrile suspension or solventless conditions, and compared to the classical nitrosating system NaNO2 + CF3COOH (TFA), the latter being quite less efficient in terms of either

  用气态NO + O 2将N-氨基甲酰基氨基酸（CAA）亚硝化，这是一种有趣的合成方法，可替代光气途径，生成氨基酸N-羧基酸酐（NCA），无论是在乙腈悬浮液中还是在无溶剂的N-氨基甲酰基缬氨酸上与传统的亚硝化系统NaNO 2  + CF 3 COOH（TFA）相比，后者在速率，化学计量需求或产品的进一步可加工性方面都效率较低。NO + O 2反应的速率和效率主要取决于O 2 / NO比。评价各种亚硝化物质（N 2通过化学计量平衡的O 3，N 2 O 4，HNO 2）显示，该反应主要由N 2 O 3（对于低于0.3的O 2 / NO比率）和N 2 O 4（对于高于0.4的O 2 / NO比率）进行。（随后形成的）HNO 2的相对贡献始终保持很小。通过HNO 2（来自NaNO 2  + TFA），气态N 2 O 4或气态N 2 O 3的固相反应的差示扫描量热法（DSC）监控提供了相关的速率常数（分别在25°C时约为0
• 2-Substitute
  申请人：Pfizer Inc.

  公开号：US04224329A1

  公开（公告）日：1980-09-23

  2-Substituted-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles of the formula (I): ##STR1## and the pharmaceutically-acceptable salts thereof, wherein the hydrogen atoms in the 4a position and 9b positions are in a trans relationship to each other and the 5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole moiety is dextrorotatory; X.sub.1 and Y.sub.1 are the same or different and are each hydrogen or fluoro; Z.sub.1 is hydrogen, fluoro or methoxy; M is a member selected from the group consisting of ##STR2## a mixture thereof and C.dbd.O and n is 3 or 4; their use as tranquilizing agents, pharmaceutical compositions containing them and a process for their production.

  2-取代-5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶并[4,3-b]吲哚的化学式(I)如下：##STR1##及其药用可接受的盐，其中4a位置和9b位置的氢原子相对于彼此是反式的，而5-芳基-2,3,4,4a,5,9b-六氢-1H-吡啶并[4,3-b]吲哚基团是右旋的；X.sub.1和Y.sub.1相同或不同，分别是氢或氟；Z.sub.1是氢、氟或甲氧基；M是从下列组中选择的成员之一##STR2##或其混合物和C.dbd.O，n为3或4；它们作为镇静剂的用途，含有它们的药物组合物以及它们的生产方法。
• Microwave-Assisted Synthesis of N-Monosubstituted Urea Derivatives
  作者：Lidia De Luca、Andrea Porcheddu、Giampaolo Giacomelli、Irene Murgia

  DOI：10.1055/s-0030-1258553

  日期：2010.10

  An easy and rapid procedure for the preparation of N-monosubstituted ureas via reaction between potassium cyanate and a wide range of amines is described. The procedure was performed under microwave irradiation using water as solvent. This methodology is particularly attractive since it provides ureas in high yield and purity.

  描述了一种通过氰酸钾和多种胺之间的反应制备 N-单取代脲的简单快速的方法。该程序在微波辐射下使用水作为溶剂进行。这种方法特别有吸引力，因为它提供了高产率和纯度的尿素。
• Synthesis of 1S,5R- and 1R,5S-glycoluriles by diastereospecific α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one
  作者：Il’ya E. Chikunov、Angelina N. Kravchenko、Pavel A. Belyakov、Konstantin A. Lyssenko、Vladimir V. Baranov、Oleg V. Lebedev、Nina N. Makhova

  DOI：10.1070/mc2004v014n06abeh002050

  日期：2004.1

  A diastereospecific method for the synthesis of individual enantiomers of 1S,5R- and 1R,5S-glycoluriles has been developed based on the α-ureidoalkylation of (S)/(R)-N-carbamoyl-α-amino acids with 4,5-dihydroxyimidazolidin-2-one.

  基于（S）/（R）-N-氨基甲酰基-α-氨基酸与4,5的α-脲基烷基化反应，开发了一种非对映体特异性的方法，用于合成1S，5R-和1R，5S-糖醇的单个对映体-二羟基咪唑烷基-2-酮。