(R)-N-[(2,6-dimethylphenoxy)ethyl]-2-aminopropan-1-ol | 1254734-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-N-[(2,6-dimethylphenoxy)ethyl]-2-aminopropan-1-ol
• 英文别名: (R)-N-[2-(2,6-dimethylphenoxy)ethyl]-2-aminopropan-1-ol；R-(-)-2-([2-(2,6-dimethylphenoxy)ethyl]amino)-1-propanol；(2R)-2-[2-(2,6-dimethylphenoxy)ethylamino]propan-1-ol
• CAS: 1254734-10-5
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: SRNBWPJCLMSVQW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-[(2,6-dimethylphenoxy)ethyl]-2-aminopropan-1-ol 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 (R)-N-[(2,6-dimethylphenoxy)ethyl]-2-aminopropan-1-ol hydrochloride
  参考文献：
  名称：

  N-[(2,6-Dimethylphenoxy)alkyl]aminoalkanols—their physicochemical and anticonvulsant properties

  摘要：

  Twenty four new N-[(dimethylphenoxy) alkyl] aminoalkanols have been synthesized and evaluated for anticonvulsant activity in a series of in vivo tests: the maximum electroshock (MES), 6 Hz, and subcutaneous metrazole (ScMet). The compounds were also evaluated for possible neurotoxicity in the rotarod test. The majority of the achieved compounds exhibit quantified anticonvulsant activity. The most active compound 4: R-(-)-2N-[(2,6-dimethylphenoxy) ethyl] aminopropan-1-ol is active in MES with ED50 = 5.34 (male mice, ip), 22.28 (female mice, ip), 51.19 (male mice, po), 7.43 (rats, ip), and 28.60 (rats, po). Thermal analysis proved that its hydrochloride (4a) can exist in polymorphic forms. The compound binds to sigma, 5-HT1A, and alpha(2) receptors as well as 5-HT transporter and it does not exhibit mutagenic properties. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.045

文献信息

• The conformational analyses of 2-amino-<i>N</i>-[2-(dimethylphenoxy)ethyl]propan-1-ol derivatives in different environments
  作者：Wojciech Nitek、Agnieszka Kania、Henryk Marona、Anna M. Waszkielewicz、Ewa Żesławska

  DOI：10.1107/s2053229620008244

  日期：2020.7.1

  Four crystal structures of 2-amino-N-(dimethylphenoxyethyl)propan-1-ol derivatives, characterized by X-ray diffraction analysis, are reported. The free base (R,S)-2-amino-N-[2-(2,3-dimethylphenoxy)ethyl]propan-1-ol, C₁₃H₂₁NO₂, 1, crystallizes in the space group P2₁/n, with two independent molecules in the asymmetric unit. The hydrochloride, (S)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium chloride, C₁₃H₂₂NO₂ ⁺·Cl⁻, 2c, crystallizes in the space group P2₁, with one cation and one chloride anion in the asymmetric unit. The asymmetric unit of two salts of 2-picolinic acid, namely, (R,S)-N-[2-(2,3-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate, C₁₃H₂₂NO₂ ⁺·C₆H₄NO₂ ⁻, 1p, and (R)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate, C₁₃H₂₂NO₂ ⁺·C₆H₄NO₂ ⁻, 2p, consists of one cation and one 2-picolinate anion. Salt 1p crystallizes in the triclinic centrosymmetric space group P\overline 1, while salt 2p crystallizes in the space group P4₁2₁2. The conformations of the amine fragments are contrasted and that of 2p is found to have an unusual antiperiplanar arrangement about the ether group. The crystal packing of 1 and 2c is dominated by hydrogen-bonded chains, while the structures of the 2-picolinate salts have hydrogen-bonded rings as the major features. In both salts with 2-picolinic acid, the specific R ₁ ²(5) hydrogen-bonding motif is observed. Structural studies have been enriched by the generation of fingerprint plots derived from Hirshfeld surfaces.

  报告了四种 2-氨基-N-(二甲基苯氧乙基)丙-1-醇衍生物的晶体结构，并通过 X 射线衍射分析对其进行了表征。游离碱 (R,S)-2-氨基-N-[2-(2,3-二甲基苯氧基)乙基]丙-1-醇，C13H21NO2，1，在空间群 P21/n 中结晶，不对称单元中有两个独立的分子。盐酸盐，(S)-N-[2-(2,6-二甲基苯氧基)乙基]-1-羟基丙-2-铵氯化物，C13H22NO2 +-Cl-，2c，在空间群 P21 中结晶，不对称单元中有一个阳离子和一个氯阴离子。两种 2-吡啶甲酸盐的不对称单元，即 (R,S)-N-[2-(2,3-二甲基苯氧基)乙基]-1-羟基丙-2-氨基吡啶-2-羧酸盐 C13H22NO2 +-C6H4NO2-, 2c, 结晶在空间群 P21 中，不对称单元中有一个阳离子和一个氯阴离子。 +-C6H4NO2 -，1p，和(R)-N-[2-(2,6-二甲基苯氧基)乙基]-1-羟基丙-2-氨基吡啶-2-羧酸盐，C13H22NO2 +-C6H4NO2 -盐 1p 由一个阳离子和一个 2-苦味酸阴离子组成。盐 1p 在三菱中心对称空间群 P\overline 1 中结晶，而盐 2p 在空间群 P41212 中结晶。对胺片段的构象进行了对比，发现 2p 的胺片段在醚基上具有不寻常的反平行排列。1 和 2c 的晶体结构以氢键链为主，而 2-吡啶甲酸盐的结构则以氢键环为主。在这两种含有 2-吡啶甲酸的盐中，特定的 R 1 2(5) 氢键结构。从 Hirshfeld 表面生成的指纹图谱丰富了结构研究的内容。
• DERIVATIVES OF AMINOALKANOLS, METHOD OF OBTAINING OF AMINOALKANOLS AND THEIR USE
  申请人：Marona Henryk

  公开号：US20110028562A1

  公开（公告）日：2011-02-03

  The subject of the invention is a group of new derivatives of aminoalkaπols, more specifically [(phenoxy)alkyl]aminoalkanols and [(phenoxy)acyl)aminoalkanols, their method of obtaining and their use for production of a medicine which is used in the prophylaxis, prevention and/or treatment of diseases or symptoms having neurological background and for production of a medicine with anticonvulsant activity, which is used in seizures of various origin, also in the limbic system, in myoclonic or sound-induced seizures, in psychomotor epilepsy, as well as in relieving neuropathic or inflammatory pain.

  本发明涉及一组新的氨基烷醇衍生物，更具体地是[(苯氧基)烷基]氨基烷醇和[(苯氧基)酰基)氨基烷醇，它们的获取方法以及它们用于生产用于预防、预防和/或治疗具有神经学背景的疾病或症状的药物，以及用于生产具有抗惊厥活性的药物，用于各种起源的癫痫发作，也用于边缘系统、肌阵挛或声音诱发的癫痫发作、精神运动性癫痫，以及缓解神经病性或炎症性疼痛。
• Supramolecular architectures of succinates of 1-hydroxypropan-2-aminium derivatives
  作者：Ewa Żesławska、Wojciech Nitek、Henryk Marona、Anna M. Waszkielewicz

  DOI：10.1107/s2053229618008574

  日期：2018.7.1

  with four cations and two anions in the asymmetric unit. The hydroxy group of the cation of 1s is observed in two R/S disorder positions. The crystals of these two salts display similar supramolecular architectures (i.e. two‐dimensional networks), built mainly by intermolecular N+—H…Oδ− and O—H…Oδ− hydrogen bonds, where `δ−' represents a partial charge. The succinate anions are engaged in hydrogen

  氨基链烷醇和芳氧基烷基衍生物被称为潜在的抗惊厥药。两种新的盐，即双（R，S）‐ N- [2-（2,6-二甲基苯氧基）乙基] -1-羟基丙烷-2-铵}琥珀酸盐（1s），C 13 H 22 NO 2 + ·0.5 C 4 H 4 O 4 2−和bis （S）‐（+）‐ N‐ [2-（2,6-二甲基苯氧基）乙基] ‐1‐羟基丙烷‐2‐}}琥珀酸酯（2s），C 13 H 22 NO 2 + ·0.5C 4 H 4 O 4 2−通过单晶X射线衍射制备并表征。N原子通过从琥珀酸转移质子而质子化。盐1s在P 2 1 / n的空间群中以一个阳离子和一半阴离子在一个反对称中心上结晶，而（2s）在P 2 1的空间群中以四个阳离子和两个阴离子在非对称单元中结晶。。在两个R / S无序位置观察到1s阳离子的羟基。这两种盐的晶体显示出相似的超分子结构（即二维网络），主要由分子间的N + -H… Oδ-和O-H
• US8633251B2
  申请人：——

  公开号：US8633251B2

  公开（公告）日：2014-01-21
• US8841347B2
  申请人：——

  公开号：US8841347B2

  公开（公告）日：2014-09-23