(S)-1-羟基-1-(4-羟基苯基)-2-氨基乙烷 | 826-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (S)-1-羟基-1-(4-羟基苯基)-2-氨基乙烷
• 英文名称: (S)-1-hydroxy-1-(4-hydroxyphenyl)-2-aminoethane
• 英文别名: (+)-Octopamine；(S)-octopamine；octopamine；(S)-2-amino-1-(4-hydroxyphenyl)ethanol；(+)-2-Amino-1-(4-hydroxy-phenyl)-ethanol；Octopamin；4-[(1S)-2-amino-1-hydroxyethyl]phenol
• CAS: 826-01-7
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: QHGUCRYDKWKLMG-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 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

反应信息

• 作为反应物：
  描述：

  (S)-1-羟基-1-(4-羟基苯基)-2-氨基乙烷 生成 4-[(1S)-2-[[(Z)-1-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethylamino]-2-nitroethenyl]amino]-1-hydroxyethyl]phenol
  参考文献：
  名称：

  HIRAI, SHIRO;HIRANO, HIROSHI;ARAI, HIROTOSHI;KIBA, YASUO;SHIBATA, HISANAR+

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(+)-acetic acid 4-(2-benzyloxycarbonylamino-1-hydroxy-ethyl)phenyl ester 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 (S)-1-羟基-1-(4-羟基苯基)-2-氨基乙烷
  参考文献：
  名称：

  Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells

  摘要：

  The selective induction of death in cancer cells is a major challenge in modern medicine. In this communication we describe the synthesis of an 88-membered combinatorial library, and the subsequent evaluation of these compounds for their ability to selectively induce apoptosis in cancerous cells. A compound was identified from the library that induces apoptosis in U-937 and HL-60 cell lines. This compound is a remarkably selective pro-apoptotic agent for these cancer cell lines, as it does not induce significant death in noncancerous white blood cells, even at concentrations as high as 1000 muM.

  DOI：

  10.1021/ja038043d

文献信息

• Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein
  作者：Inha Cho、Christopher K. Prier、Zhi‐Jun Jia、Ruijie K. Zhang、Tamás Görbe、Frances H. Arnold

  DOI：10.1002/anie.201812968

  日期：2019.3.4

  Chiral 1,2‐amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable

  从神经递质到抗病毒剂的生物活性化合物中广泛存在手性1,2-氨基醇。尽管已经开发出许多用于获得氨基醇的合成方法，但是烯烃直接氨基羟基化为未保护的，对映体富集的氨基醇仍然是一个挑战。使用定向进化，我们设计了一种基于热稳定细胞色素c的血红蛋白生物催化剂，该生物色素在厌氧条件下使用O将烯烃直接以高对映选择性（高达2500 TTN和90％ee）转化为氨基醇。新戊酰羟胺作为胺化剂。建议该反应通过在酶活性位点产生的反应性铁氮物种进行，从而可以通过蛋白质工程调节催化剂的活性和选择性。
• Highly Enantioselective Henry Reactions in Water Catalyzed by a Copper Tertiary Amine Complex and Applied in the Synthesis of (S)-N-trans-Feruloyl Octopamine
  作者：Guoyin Lai、Fengfeng Guo、Yueqin Zheng、Yang Fang、Haigang Song、Kun Xu、Sujing Wang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1002/chem.201002915

  日期：2011.1.24

  It's in the water! A new copper tertiary amine complex was prepared and applied in asymmetric Henry reactions in water and in the short synthesis of (S)‐N‐trans‐feruloyl octopamine. This catalytic system provided an approach to the enantioselective Henry reaction of aldehydes with hydroxyl substituents (see graphic).

  在水里！制备了一种新的铜叔胺络合物，并将其用于水中的不对称亨利反应中，以及在短时间内合成（S）-N-反式-阿魏酸八胺的过程中。该催化体系为醛与羟基取代基的对映选择性亨利反应提供了一种方法（见图）。
• Synthesis of Aromatic 1,2-Amino Alcohols Utilizing a Bienzymatic Dynamic Kinetic Asymmetric Transformation
  作者：Johannes Steinreiber、Martin Schürmann、Friso van Assema、Michael Wolberg、Kateryna Fesko、Christoph Reisinger、Daniel Mink、Herfried Griengl

  DOI：10.1002/adsc.200700051

  日期：2007.6.4

  The applicability of the recent published bienzymatic protocol for the synthesis of (R)-2-amino-1-phenylethanol was tested using L-threonine aldolase from Pseudomonas putida and l-tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efi1, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine

  对的（合成的最近出版bienzymatic协议的适用性- [R）-2-氨基-1-苯基-乙醇使用从L-苏氨酸醛缩酶试验恶臭假单胞菌和L-酪氨酸脱羧酶从任一粪肠球菌（EFA），或从两个基因肠球菌屎肠球菌（EFI1，EFI2）。在所有21种苯甲醛衍生物中均进行了初步TLC筛选。使用Efi1以小规模获得章鱼胺和去甲肾上腺素作为（S）-对映体。三种方案均按规模生产，可产生对映体富集的（S）-章鱼胺（产率99％，ee 81％），（R）-2-氨基-1-苯基乙醇（产率61％，ee62％）和（S）-去甲肾上腺素（收率76％，ee 79％）。
• Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia
  作者：Michele L. R. Heffernan、Lee W. Herman、Scott Brown、Philip G. Jones、Liming Shao、Michael C. Hewitt、John E. Campbell、Nina Dedic、Seth C. Hopkins、Kenneth S. Koblan、Linghong Xie

  DOI：10.1021/acsmedchemlett.1c00527

  日期：2022.1.13

  (SEP-363856) is a trace-amine associated receptor 1 (TAAR1) agonist with 5-HT1A receptor agonist activity in Phase 3 clinical development, with FDA Breakthrough Therapy Designation, for the treatment of schizophrenia. TAAR1 is a G-protein-coupled receptor (GPCR) that is expressed in cortical, limbic, and midbrain monoaminergic regions. It is activated by endogenous trace amines, and is believed to play

  Ulotaront (SEP-363856) 是一种微量胺相关受体 1 (TAAR1) 激动剂，具有 5-HT1A 受体激动剂活性，处于 3 期临床开发阶段，获得 FDA 突破性治疗指定，用于治疗精神分裂症。TAAR1 是一种 G 蛋白偶联受体 (GPCR)，在皮质、边缘和中脑单胺能区域表达。它被内源性微量胺激活，并被认为在调节多巴胺能、5-羟色胺能和谷氨酸能回路中起重要作用。本文报道了 ulotaront 及其类似物与内源性 TAAR1 激动剂相比的 TAAR1 激动数据。此外，围绕 ulotaront 建立了人类 TAAR1 同源模型，以识别关键相互作用并试图更好地了解支架特异性 TAAR1 激动剂的结构-活性关系。
• PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED BETA-AMINO ALCOLHOLS STARTING FROM GLYCINE AND AN ALDEHYDE IN THE PRESENCE OF A THREONINE ALDOLASE AND A DECARBOXYLASE
  申请人：Schürmann Martin

  公开号：US20100068771A1

  公开（公告）日：2010-03-18

  The invention relates to a process for the preparation of an enantiomerically enriched β-amino alcohol, wherein glycine or a glycine salt and an aldehyde are reacted in the presence of a threonine aldolase and a decarboxylase to form the corresponding enantiomerically enriched β-aminoalcohol, and wherein at least either the threonine aldolase or the decarboxylase is β-selective. In a preferred embodiment of the invention at least either the threonine aldolase or the decarboxylase is enantioselective.

  该发明涉及一种制备对映富集的β-氨基醇的方法，其中在苏氨酸醛缩酶和脱羧酶的存在下，甘氨酸或甘氨酸盐和醛反应，形成相应的对映富集的β-氨基醇，其中至少苏氨酸醛缩酶或脱羧酶之一是β-选择性的。在该发明的优选实施方式中，至少苏氨酸醛缩酶或脱羧酶之一是对映选择性的。