4-(2-Amino-2-hydroxyethyl)phenol | 356561-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-Amino-2-hydroxyethyl)phenol
• CAS: 356561-03-0
• 化学式: C₈H₁₁NO₂
• 分子量: 153.18
• InChiKey: NVLWXTQBTLBRJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

文献信息

• [EN] PROCESS FOR THE PREPARATION OF RACTOPAMINE HYDROCHLORIDE VIA NOVEL INTERMEDIATES<br/>[FR] PROCÉDÉ DE PRÉPARATION DU CHLORHYDRATE DE RACTOPAMINE PAR LE BIAIS DE NOUVEAUX INTERMÉDIAIRES
  申请人：INCHEM LABORATORIES PVT LTD

  公开号：WO2020229935A1

  公开（公告）日：2020-11-19

  The present disclosure describes the new methods of preparation of Ractopamine which are superior to state of art by involving comparatively better and mild reaction conditions. The method of preparation involves following steps: In the first embodiment, 4-(4-hydroxyphenyl)-3-butene-2-one is prepared by condensation of 4-hydroxybenzaldehyde with acetone in the presence of sodium hydroxide/hydrochloric acid. In the next step, 4-(4-hydroxyphenyl)-3-butene-2-one undergoes hydrozination with 4-(-2-amino-1- hydroxyl ethyl) phenolhydrochloride in the presence of base using Pd/C/H2 as a catalyst in methanol/ethanol as solvent to yield Ractopamine base. In another embodiment, advancement over the previous scheme is use of Raney Ni/H2 instead of Pd/C as a catalyst. In yet another embodiment, 2-amino-1-(4-hydroxyphenyl) ethanone hydrochloride reacts with 4-(4-hydroxyphenyl)-butane -2-one in the presence of base and raney nickel/H2 as a catalyst. Compared to the prior art reports where Pd/C was used as a catalyst, Raney Ni is used in the present embodiment which is comparatively economical and better catalyst.

  本公开描述了制备雷克托巴胺的新方法，这些方法优于现有技术，因为涉及相对更好和温和的反应条件。制备方法涉及以下步骤：在第一实施例中，通过在氢氧化钠/盐酸存在下，将对羟基苯甲醛与丙酮缩合制备4-(4-羟基苯基)-3-丁烯-2-酮。在接下来的步骤中，4-(4-羟基苯基)-3-丁烯-2-酮在碱存在下与4-(-2-氨基-1-羟基乙基)苯酚盐酸盐进行氢化反应，使用Pd/C/H2作为催化剂，甲醇/乙醇作为溶剂，得到雷克托巴胺碱。在另一实施例中，相对于先前方案的进展是使用Raney Ni/H2而不是Pd/C作为催化剂。在另一实施例中，2-氨基-1-(4-羟基苯基)乙酮盐酸盐在碱和Raney镍/H2作为催化剂的存在下与4-(4-羟基苯基)-丁烷-2-酮发生反应。与先前报道中使用Pd/C作为催化剂的情况相比，本实施例中使用相对经济且更好的Raney Ni作为催化剂。
• Process for the optical resolution of racemic mixtures of alpha-naphthyl-propionic acids
  申请人：Alfa Chemicals Italiana S.r.l.

  公开号：EP0143371A1

  公开（公告）日：1985-06-05

  A new process for the optical resolution of racemic mixtures of α-naphthyl-propionic acids of formula This process comprises reacting a racemic mixture of a compound of formula with an optically active substance of formula R4-NH2 (III), said substance being a β-aminoalcohol, thus forming a pair of diastereoisomeric amides which are resolved into the single diastereoisomers by fractional crystallization. The obtained single diastereoisomeric amide is then hydrolized to give the desired optically active α-naphthyl-propionic acid of formula In the above compound I → III and VI, R, is (C1-6)alkyl, R2 stands for hydrogen, halogen, mercapto, (C1-6)alkylthio, phenylthio, benzylthio (C1-6)alkylsulfonyl, benzenesulfonyl, benzenesulfonyl substituted by halogen or (C1-4)alkyl, R3 is a reactive group and R4 is the residue of a primary or secondary alcohol.

  式α-萘基丙酸外消旋混合物的光学解析新工艺 该工艺包括将一种式化合物的外消旋混合物与一种式 R4-NH2 (III) 的光学活性物质反应。 与一种光学活性物质 R4-NH2 (III)（所述物质为 β-氨基醇）反应，从而形成一对非对映异构体酰胺，通过分馏结晶将其分解为单一非对映 异构体。然后将得到的单一非对映异构体酰胺水解，得到所需的光学活性 α-萘基丙酸，其式为 在上述化合物Ⅰ→Ⅲ和Ⅵ中，R是(C1-6)烷基，R2代表氢、卤素、巯基、(C1-6)烷硫基、苯硫基、苄硫基、(C1-6)烷磺酰基、苯磺酰基、被卤素或(C1-4)烷基取代的苯磺酰基，R3是活性基团，R4是伯醇或仲醇的残基。
• Process for the optical resolution of racemic mixtures of alpha-naphtyl-propionic acids
  申请人：ALFA WASSERMANN S.p.A.

  公开号：EP0182279A1

  公开（公告）日：1986-05-28

  A new process for the optical resolution of racemic mixtures of a-naphthyl-propionic acids of formula where R, is an alkyl group, straight or branched, having from 1 to 6 carbon atoms and R2 represents an hydrogen or an halogen atom. This process comprises reacting a racemic mixture of a compound of formula II wherein R1 and R2 have the above seen meanings and R3 is a reactive group, with an optically active compound of formula wherein R4 is the residue of a primary or secondary alcohol which, taken with the NH2 radical, forms an optically active β-aminoalcohol, to give a pair of diastereoisomeric amides of formula [d,d + 1,d] or [d,1 + 1,1] wherein R1, R2 and R4 have the above seen meanings, which is resolved into the single diastereoisomeric amides of formula d,d or 1,d or d,1 or 1,1 The compounds of formula V, by means of a subsequent acid hydrolysis give the optically active a-naphthyl-propionic acids of formula d or 1 wherein R1 and R2 have the above seen meanings.

  一种光学解析式 a-萘基丙酸外消旋混合物的新工艺 其中，R 是具有 1 至 6 个碳原子的直链或支链烷基，R2 代表氢原子或卤素原子。 该工艺包括使式 II 的化合物的外消旋混合物反应 其中 R1 和 R2 具有上述含义，R3 为活性基团，与式 II 的光学活性化合物的外消旋混合物反应。 其中 R4 是伯醇或仲醇的残基，它与 NH2 基形成光学活性的 β-氨基醇，从而得到一对非对映异构的式酰胺。 [d,d+1,d]或[d,1+1,1]，其中 R1、R2 和 R4 具有上述含义。 d,d 或 1,d 或 d,1 或 1,1 通过随后的酸水解，式 V 的化合物可得到具有光学活性的式 a-萘基丙酸 d或1 其中 R1 和 R2 具有上述含义。
• METHOD OF MEASUREMENT OF MATERIAL AND TESTPIECE
  申请人：KABUSHIKI KAISHA KYOTO DAIICHI KAGAKU

  公开号：EP0860695A1

  公开（公告）日：1998-08-26

  A method of measuring an analyte, comprising a step of measuring a detectable substance by using a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein a layered inorganic compound is caused to exist in the reaction system including the formation reaction of the detectable substance, whereby high-sensitivity measurement is made possible, the detectable substance can be stabilized to improve accuracy of the measurement, a rate of a chemical reaction is increased to enable quick measurement, and high-sensitivity measurement is made possible even in a reaction system which forms an insoluble substance. Also, it can be provided an analytical testing piece for measuring an analyte, by measuring a detectable substance by using a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein the testing piece comprises at least one test portion having a detection portion for detecting the detectable substance and contains a layered inorganic compound at least in the test portion, whereby diffusion and elution of a dyestuff or the like is prevented, more sensitive and accurate simple analysis is made possible, and easy handling is possible.

  一种测量被分析物的方法，包括以下步骤：根据样品中含有的被分析物的化学反应，使用包括可检测物质的形成反应的反应系统测量可检测物质，其中在包括可检测物质的形成反应的反应系统中导致层状无机化合物的存在、从而实现高灵敏度测量，稳定可检测物质以提高测量精度，提高化学反应速率以实现快速测量，即使在形成不溶性物质的反应体系中也能实现高灵敏度测量。此外，还可以提供一种用于测量被分析物的分析检测件，通过使用反应系统测量可检测物质，该反应系统包括基于样品中所含被分析物的化学反应的可检测物质的形成反应，其中检测件包括至少一个测试部分，该测试部分具有用于检测可检测物质的检测部分，并且至少在测试部分中包含分层无机化合物，从而防止染料或类似物的扩散和洗脱，实现更灵敏、更准确的简单分析，并且易于处理。
• N-substituted oligomers and methods for their synthesis, e.g. polyglycine bearing nucleic acid bases
  申请人：CHIRON CORPORATION

  公开号：EP1258492A1

  公开（公告）日：2002-11-20

  Poly N-substituted Glycines (poly NSGs), wherein the substituents bear purine or pyrimidine bases (R9) every second glycine: In addition, a solid phase method for the synthesis of N-substituted oligomers of more general structures is disclosed.The poly NSGs obtainable by this method can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two "sub-monomers" directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a resin-bound α-haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using the automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability.

  聚 N-取代甘氨酸（poly NSGs），其中每第二个甘氨酸的取代基都带有嘌呤或嘧啶碱（R9）： 此外，还公开了一种用于合成更一般结构的 N-取代低聚物的固相方法。通过这种方法获得的聚 NSG 可以具有多种侧链取代基。每个 N-取代甘氨酸单体由两个 "子单体 "直接在固体支持物上组装而成。每个单体加成循环包括两个步骤：(1) 用包含能被 -NH2 亲核置换的离去基团（如卤乙酸）的酰化剂将与载体结合的仲胺酰化，以及 (2) 通过离去基团的亲核置换引入侧链、(2) 通过亲核置换离去基团，如卤素（作为与树脂结合的 α-卤代乙酰胺）和足量的包含 -NH2 基团的第二亚单体，如伯胺、烷氧基胺、半肼、酰肼、肼基脲或类似物，引入侧链。重复酰化和置换两步循环，即可得到所需的低聚物。利用本方法的自动合成技术可高效合成多种低聚 NSG，这使得这些低聚物在生成和快速筛选各种肽模拟库方面具有吸引力。本发明公开的低聚物，如 N-取代甘氨酸（即多 NSG），提供了一类新的肽类化合物，这类化合物在自然界中并不存在，但可以通过合成获得，而且已被证明具有显著的生物活性和蛋白水解稳定性。