N-acetyl-N-4-hydroxyphenylglycine | 119656-42-7

• 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: N-acetyl-N-4-hydroxyphenylglycine
• 英文别名: N-acetyl-L-4-hydroxyphenylglycine；Glycine, N-acetyl-N-(4-hydroxyphenyl)-；2-(N-acetyl-4-hydroxyanilino)acetic acid
• CAS: 119656-42-7
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: XZFYOMHRTSFFJG-UHFFFAOYSA-N

物化性质

• 沸点：
  457.6±30.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-((4-hydroxyphenyl)amino)acetonitrile 在 sodium hydroxide 、 乙醚 作用下， 生成 N-acetyl-N-4-hydroxyphenylglycine
  参考文献：
  名称：

  Shimo, Bulletin of the Chemical Society of Japan, 1926, vol. 1, p. 228

  摘要：

  DOI：

文献信息

• Process for manufacturing N-acyl derivatives of hydroxy-arylglycines
  申请人：Nobel Hoechst Chimie

  公开号：US04105690A1

  公开（公告）日：1978-08-08

  Condensation of the addition product of glyoxylic acid and amides with hydroxyaryl compounds is effected by a first step, wherein the reaction is carried out hot, at a temperature below 60.degree. C, of an aliphatic amide having at the most 4 carbon atoms selected from the group of acetamide, chloracetamide, propionamide, acrylamide and butyramide, on an aqueous solution of glyoxylic acid. Then in a second step, after the addition of acetic acid and gaseous hydrochloric acid, condensation is effected at a temperature below 35.degree. C of the carboxamidoglycolic acid with an excess reaching 500% of hydroxyaryl compound selected from the group comprising phenol and its alkyl derivatives, their halogen derivatives, polyphenols and their ethers and betanaphthol. After the condensation of said second step, the volatile products are removed by vacuum distillation. When the hydroxyaryl compound is phenol, the crude product resulting from this distillation is taken up in nitromethane or water, which are a non-solvent of the N-acyl derivative of parahydroxyphenylglycine but a solvent of the corresponding ortho derivative; the proportion of the para derivative in the resulting compound is then of the order of 100%.

  甘氨酸和酰胺的加成产物与羟基芳基化合物的缩合作用是通过第一步实现的，其中反应在高温下进行，温度低于60摄氏度，在含有甘氨酸的水溶液中，作用于最多含有4个碳原子的脂肪酰胺，所述脂肪酰胺选自乙酰胺、氯乙酰胺、丙酰胺、丙烯酰胺和丁酰胺。然后，在第二步中，在加入乙酸和气态盐酸后，在温度低于35摄氏度下，将羧胺基甘氨酸与羟基芳基化合物缩合，所述缩合物中羟基芳基化合物的过量达到羟基芳基化合物的500%，所述羟基芳基化合物选自苯酚及其烷基衍生物、卤代衍生物、多酚及其醚和β-萘酚。在第二步的缩合后，通过真空蒸馏去除挥发性产物。当羟基芳基化合物为苯酚时，通过硝基甲烷或水将此蒸馏得到的粗产品溶解，硝基甲烷或水是对邻羟基苯甘氨酸的非溶剂但是对相应的邻位衍生物是溶剂；因此所得化合物中对位衍生物的比例约为100%。
• Stereoselective resolution of phenylglycine derivatives with enzyme
  申请人：Bayer Aktiengesellschaft

  公开号：US04439524A1

  公开（公告）日：1984-03-27

  The invention relates to a process for the stereo-selective resolution of DL-phenylglycine derivatives by hydrolyzing the ester or amide groups of N-acyl-L-phenylglycine esters or amides in N-acyl-DL-phenylglycine esters or amides by the action of enzymes, separating the N-acyl-D-phenylglycine esters or amides from the N-acyl-L-phenylglycines and then, if appropriate, subjecting the ester or amide groups of the D-enantiomers and the acyl groups to acid hydrolysis, characterized in that enzyme which are bonded to carriers are allowed to act on the N-acyl-DL-phenylglycine esters or amides in an inert two-phase mixture consisting of water-immiscible organic solvent and water.

  该发明涉及一种通过水解N-酰基-L-苯基甘氨酸酯或酰胺的酯或酰胺基团来进行DL-苯基甘氨酸衍生物的立体选择性分离的方法，方法是通过酶的作用，将N-酰基-DL-苯基甘氨酸酯或酰胺中的酯或酰胺基团水解，将N-酰基-D-苯基甘氨酸酯或酰胺与N-酰基-L-苯基甘氨酸分离开来，然后，如果适当的话，将D-对映体和酰基的酯或酰胺基团进行酸水解，其特点在于将结合到载体上的酶允许作用于由水不相溶有机溶剂和水组成的惰性两相混合物中的N-酰基-DL-苯基甘氨酸酯或酰胺。
• AROMATIC COMPOUND
  申请人：FUKUSHIMA Tae

  公开号：US20120238750A1

  公开（公告）日：2012-09-20

  The compound of the present invention is represented by the following general formula (1): [wherein X 1 represents a nitrogen atom or a group —CH═; R 1 represents a group —Z—R 6 , wherein Z represents a group —CO—, a group —CH(OH)—, or the like, and R 6 represents a 5- to 15-membered monocyclic, dicyclic, or tricyclic, saturated or unsaturated heterocyclic group having 1 to 4 nitrogen atoms, oxygen atoms, or sulfur atoms; R 2 represents a hydrogen atom, a halogen atom or a lower alkylene group; Y represents a group —O—, a group —CO—, a group —CH(OH)—, a lower alkylene group, or the like; and A represents a group or the like, wherein R 3 represents a hydrogen atom, a lower alkoxy group, or the like, p represents 1 or 2, and R 4 represents an imidazolyl lower alkyl group or the like.

  本发明的化合物由以下通式（1）表示：[其中X1表示氮原子或基团—CH═; R1表示基团—Z—R6，其中Z表示基团—CO—、基团—CH（OH）—或类似物，而R6表示具有1至4个氮原子、氧原子或硫原子的5至15环的单环、双环或三环、饱和或不饱和的杂环基团; R2表示氢原子、卤素原子或较低的烷基链; Y表示基团—O—、基团—CO—、基团—CH（OH）—、较低的烷基链或类似物; A表示基团或类似物，其中R3表示氢原子、较低的烷氧基或类似物，p表示1或2，而R4表示咪唑基较低的烷基链或类似物。
• Stereoselektive Spaltung von Phenylglycinderivaten und 4-Hydroxyphenylglycinderivaten mit Enzymharzen
  申请人：BAYER AG

  公开号：EP0003786A1

  公开（公告）日：1979-09-05

  Die stereoselektive Spaltung von DL-Phenylglycinderivaten durch Hydrolyse der Ester- oder Amidgruppe an N-Acyl-L-phenylglycinestern oder -amiden in N-Acyl-DL-phenylglycinestern oder -amiden durch Einwirkung von Enzymen, Trennung der N-Acyl-D-phenylglycinester oder -amide von den N-Acyl-L-phenylglycinen und gegebenenfalls anschließende saure Hydrolyse der Ester- oder Amidgruppen der D-Enantiomeren sowie der Acylgruppen, wird dadurch verbessert, daß man das Substrat in Lösung vorlegt und das Enzym trägergebunden einsetzt.

  在酶的作用下，通过水解 N-酰基-L-苯甘氨酸酯或酰胺中 N-酰基-DL-苯甘氨酸酯或酰胺上的酯基或酰胺基，立体选择性地裂解 DL-苯甘氨酸衍生物、将 N-酰基-D-苯甘氨酸酯或酰胺从 N-酰基-L-苯甘氨酸酯或酰胺中分离出来，并在适当情况下对 D-对映体的酯或酰胺基团和酰基进行后续酸水解，可通过提供溶液中的底物和使用载体结合状态的酶得到改善。
• Process for the separation of a mixture of enantiomers
  申请人：DSM N.V.

  公开号：EP0838448A1

  公开（公告）日：1998-04-29

  The invention relates to a process for the preparation of a diastereomer complex and the preparation of enantiomers in optically enriched form in which one or more mixtures of enantiomers in a solvent are contacted with one or more resolving agents, yielding the diastereomer complex, and in which optionally (a mixture of) the enantiomer(s) present in the diastereomer are subsequently isolated in optically active form from the diastereomer complex. The invention further relates to a diastereomer complex comprising at least three compounds of which at least one compound is a resolving agent in optically active form and at least one compound is an enantiomer in optically active form.

  本发明涉及一种制备非对映异构体复合物和制备光学富集形式对映体的工艺，在该工艺中，溶剂中的一种或多种对映体混合物与一种或多种溶解剂接触，产生非对映异构体复合物，随后从非对映异构体复合物中选择性地分离出光学活性形式的存在于非对映异构体中的对映体（混合物）。 本发明还涉及一种非对映异构体复合物，该复合物由至少三种化合物组成，其中至少一种化合物是光学活性形式的分解剂，至少一种化合物是光学活性形式的对映体。