(RS)-2-amino-4-(4-octylphenyl)butan-1-ol | 177260-59-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (RS)-2-amino-4-(4-octylphenyl)butan-1-ol
• 英文别名: 2-amino-4-(4-octylphenyl)butanol；2-amino-4-(4-octylphenyl)butan-1-ol
• CAS: 177260-59-2
• 化学式: C₁₈H₃₁NO
• 分子量: 277.45
• InChiKey: OGNZEBJTKXTOOP-UHFFFAOYSA-N

物化性质

• 沸点：
  427.2±40.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-2-amino-4-(4-octylphenyl)butan-1-ol 在 四氮唑 、 sulfur 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 [1-(Di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057
• 作为产物：
  描述：

  1-苯基辛烷 在 盐酸 、 三乙基硅烷 、 三氯化铝 、 sodium ethanolate 、 四氯化钛 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (RS)-2-amino-4-(4-octylphenyl)butan-1-ol
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057

文献信息

• Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines
  作者：Hannah E. Askey、James D. Grayson、Joshua D. Tibbetts、Jacob C. Turner-Dore、Jake M. Holmes、Gabriele Kociok-Kohn、Gail L. Wrigley、Alexander J. Cresswell

  DOI：10.1021/jacs.1c07401

  日期：2021.10.6

  moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of its in vivo active form (by iterative α-C–H functionalization of ethanolamine). The reaction can also be sequenced

  苯乙烯的催化分子间氢氨烷基化 (HAA) 为药理学相关的 γ-芳胺提供了强大的断裂作用，但目前的方法不能利用未受保护的伯烷基胺作为原料。金属催化的 HAA 方案对胺伴侣上的 α-取代也高度敏感，并且不存在通过这种方法合成 α-叔 γ-芳胺的催化解决方案。我们报告了使用有机光氧化还原催化解决这些问题的方法，能够直接、模块化和可持续地制备α-（二）取代的γ-芳胺，包括具有挑战性的电子中性和适度富电子的芳基。可以耐受多种功能，并且反应可以在连续流程中以数克规模运行。该方法适用于重磅药物芬戈莫德及其体内活性形式的膦酸盐模拟物的简洁、无保护基合成（通过乙醇胺的迭代 α-C-H 官能化）。该反应还可以通过分子内N -芳基化进行测序，以提供获得有价值的（螺环）1,2,3,4-四氢喹啉和 1,2,3,4-四氢萘啶的通用和模块化途径。机理和动力学研究支持叠氮基自由基对烷基胺的不可逆氢原子转移活化以及自由基链
• PREPARATION OF FINGOLIMOD AND ITS SALTS
  申请人：Katkam Srinivas

  公开号：US20140235895A1

  公开（公告）日：2014-08-21

  The present application provide processes for the preparation of fingolimod and its pharmaceutically acceptable salts, process for the purification of fingolimod hydrochloride and process for the preparation of amorphous fingolimod hydrochloride.

  本申请提供了制备非格列酮及其药用可接受盐的过程，非格列酮盐酸盐的纯化过程以及非晶态非格列酮盐酸盐的制备过程。
• Benzene compound and pharmaceutical use thereof
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US05948820A1

  公开（公告）日：1999-09-07

  A benzene compound of the formula ##STR1## wherein each symbol is as defined in the specification; an optically active isomer or salt thereof, a medicinal composition containing the same, and an immunosuppressant containing the same as the active ingredient. The compound, optically active isomer or salt has an excellent immunosuppressive effect and is useful as an inhibitor for the rejection reaction occurring in organ or bone marrow transplantation, and as a preventive or remedy for articular rheumatism, atopic eczema (dermatitis), Beh.cedilla.et's disease, uveal disease, systemic lupus erythematosus, Sjogren's syndrome, multiple sclerosis, myasthenia gravis, type I diabetes, endocrine ophthalmopathy, primary biliary, cirrhosis, Crohn's disease, glomerulonephritis, sarcoidosis, psoriasis, pemphigus, aplastic anemia, idiopathic thrombocytopenic purpura, allergy, polyarteritis nodosa, progressive systemic sclerosis, mixed connective-tissue disease, aortitis syndrome, polymyositis, dermatomyositis, Wegener's granuloma, ulcerative colitis, active chronic hepatitis, autoimmune hemolytic anemia, Evans' syndrome, bronchial asthma and pollinosis. It is useful also as an antifungal agent and hair growth stimulant.

  一种苯环化合物，其化学式为##STR1## 其中每个符号如规范中定义的；其光学活性异构体或盐，含有该化合物的药物组合物，以及含有该化合物作为活性成分的免疫抑制剂。该化合物，光学活性异构体或盐具有出色的免疫抑制作用，并可用作器官或骨髓移植中发生的排斥反应的抑制剂，以及关节风湿病、特应性湿疹（皮炎）、Beh.cedilla.et病、葡萄膜疾病、系统性红斑狼疮、Sjogren综合症、多发性硬化症、重症肌无力、I型糖尿病、内分泌眼病、原发性胆汁性肝硬化、克罗恩病、肾小球肾炎、结节病、银屑病、天疱疮、再生障碍性贫血、特发性血小板减少性紫癜、过敏、多动脉炎、进行性系统性硬化、混合结缔组织病、主动脉炎综合征、多发性肌炎、皮肌炎、Wegener肉芽肿、溃疡性结肠炎、活动性慢性肝炎、自身免疫性溶血性贫血、Evans综合症、支气管哮喘和过敏性鼻炎的预防或治疗。它还可用作抗真菌剂和促进头发生长的刺激剂。
• BENZENE COMPOUND AND MEDICINAL USE THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0778263A1

  公开（公告）日：1997-06-11

  A benzene compound of the formula wherein each symbol is as defined in the specification; an optically active isomer or salt thereof, a medicinal composition containing the same, and an immunosuppressant containing the same as the active ingredient. The compound, optically active isomer or salt has an excellent immunosuppressive effect and is useful as an inhibitor for the rejection reaction occurring in organ or bone marrow transplantation, and as a preventive or remedy for articular rheumatism, atopic eczema (dermatitis), Behçet's disease, uveal disease, systemic lupus erythematosus, Sjögren's syndrome, multiple sclerosis, myasthenia gravis, type I diabetes, endocrine ophthalmopathy, primary biliary, cirrhosis, Crohn's disease, glomerulonephritis, sarcoidosis, psoriasis, pemphigus, aplastic anemia, idiopathic thrombocytopenic purpura, allergy, polyarteritis nodosa, progressive systemic sclerosis, mixed connective-tissue disease, aortitis syndrome, polymyositis, dermatomyositis, Wegener's granuloma, ulcerative colitis, active chronic hepatitis, autoimmune hemolytic anemia, Evans' syndrome, bronchial asthma and pollinosis. It is useful also as an antifungal agent and hair growth stimulant.

  式中的苯化合物 其中各符号如说明书中所定义； 其光学活性异构体或盐、含有相同物质的药物组合物，以及含有相同物质作为活性成分的免疫抑制剂。 该化合物、光学活性异构体或盐具有极佳的免疫抑制效果，可作为器官或骨髓移植中发生的排斥反应的抑制剂、可用于预防或治疗关节风湿病、特应性皮炎、白塞氏病、葡萄膜病、系统性红斑狼疮、斯约格伦综合征、多发性硬化症、重症肌无力、I 型糖尿病、内分泌性眼病原发性胆道病、肝硬化、克罗恩病、肾小球肾炎、肉瘤病、银屑病、丘疹性荨麻疹、再生障碍性贫血、特发性血小板减少性紫癜、过敏症、结节性多动脉炎、进行性系统硬化症、混合结缔组织病、大动脉炎综合征、多发性肌炎、皮肌炎、韦格纳肉芽肿、溃疡性结肠炎、活动性慢性肝炎、自身免疫性溶血性贫血、埃文斯综合征、支气管哮喘和花粉症。它还是一种有用的抗真菌剂和生发剂。
• Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit
  作者：Michio Shimamura、Naoki Okamoto、Yi-Ying Huang、Jouji Yasuoka、Kenji Morita、Akira Nishiyama、Yuusuke Amano、Tadashi Mishina

  DOI：10.1016/j.ejmech.2005.11.013

  日期：2006.5

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.