(R)-α-甲基苄磺酸 | 86963-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-α-甲基苄磺酸
• 中文别名: (R)-ALPHA-甲基苯甲烷磺酸；(R)-alpha-甲基苯甲烷磺酸；(R)-(+)-1-苯乙磺酸；(R)-α-甲基苯甲烷磺酸
• 英文名称: (R)-1-phenylethanesulfonic acid
• 英文别名: (R)-1-phenylethylsulfonic acid；(R)-1-phenyl-ethanesulfonic acid；(R)-1-Phenyl-aethansulfonsaeure；(R)-1-Phenyl-aethan-sulfonsaeure-(1)；(1R)-1-phenylethanesulfonic acid
• CAS: 86963-40-8
• 化学式: C₈H₁₀O₃S
• 分子量: 186.232
• InChiKey: COFMBBYARPOGBA-SSDOTTSWSA-N

物化性质

• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-α-甲基苄磺酸 、 1,2,3,6,7,11B-六氢-4H-吡嗪并[2,1-Alpha]异喹啉-4-酮 以 水 、 甲苯 为溶剂， 反应 0.25h， 以43.8%的产率得到(R)-1-phenethylsulfonic acid (R)-praziquantel amine
  参考文献：
  名称：

  一种(R)-吡喹酮胺盐及左旋吡喹酮的制备方 法

  摘要：

  本发明涉及一种(R)‑吡喹酮胺盐的制备方法和一种左旋吡喹酮的制备方法，(R)‑吡喹酮胺盐以消旋体吡喹酮胺与手性拆分试剂在溶剂中反应制得，其中，所述的手性拆分试剂为选自(R)‑布洛芬、(R)‑萘普生、(R)‑1‑苯乙基磺酸中的一种或多种。本发明具有原料易得、工艺简单、制备周期短、手性拆分试剂稳定、价格低和回收容易、成本低等优点。

  公开号：

  CN107151246B
• 作为产物：
  描述：

  苄磺酰氯 在 palladium diacetate 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 121.0h， 生成 (R)-α-甲基苄磺酸
  参考文献：
  名称：

  Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates

  摘要：

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.046

文献信息

• Dutch Resolution: Separationof Enantiomers with Families of Resolving Agents. A Status Report
  作者：Richard M. Kellogg、José W. Nieuwenhuijzen、K. Pouwer、Ton R. Vries、Quirinus B. Broxterman、Reinier F.P. Grimbergen、Bernard Kaptein、René M. Crois、Ellen de Wever、Karen Zwaagstra、Alexander C. van der Laan

  DOI：10.1055/s-2003-40508

  日期：——

  Dutch Resolution is the term given to the use of mixtures (families) of resolving agents in classical resolutions. In this status report an overview is given of the latest results and new (possible) families of resolving agents are introduced. The concept of families is discussed as well as the factors that come into play on use of families. Practical aspects of Dutch Resolution in particular and resolutions in general are discussed.

  荷兰决议（Dutch Resolution）是指在传统解析过程中使用混合物（族）的解析剂。在这份状态报告中，概述了最新的结果并介绍了新（可能）的解析剂族。讨论了族的概念以及在使用族时起作用的因素。特别讨论了荷兰决议的实际方面，以及一般的解析过程。
• Rh/Wudaphos-Catalyzed Asymmetric Hydrogenation of Sodium α-Arylethenylsulfonates: A Method To Access Chiral α-Arylethylsulfonic Acids
  作者：Xuguang Yin、Caiyou Chen、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.7b01021

  日期：2017.5.19

  A highly enantioselective hydrogenation of various sodium α-arylethenylsulfonates catalyzed by Rh/chiral ferrocenyl bisphosphorus ligand (Wudaphos) was successfully developed to construct a series of chiral α-arylethylsulfonic acids in the presence of CF3SO3H with full conversion and good to excellent enantioselectivity (>99% conversion, up to 96% ee) under mild reaction conditions for the first time

  Rh /手性二茂铁基双磷配体（Wudaphos）催化的各种α-芳基乙烯基磺酸钠的高对映选择性加氢成功开发，在CF 3 SO 3 H存在下，以完全转化率制备了一系列手性α-芳基乙基磺酸，良好至优异首次在温和的反应条件下进行对映选择性（> 99％转化率，高达96％ee）。而且，对照实验结果表明，α-芳基乙烯基磺酸和Wudaphos配体之间的非共价离子对相互作用在该不对称氢化系统中起重要作用。
• Process for preparation of 4-n-substituted amino-2-aza-1-oxabicyclo[3.3.0] oct-2-ene-6-carboxylic acid esters and process for preparation of their intermediates
  申请人：——

  公开号：US20040121482A1

  公开（公告）日：2004-06-24

  4-N-substituted amino-2-aza-1-oxabicyclo[3.3.0]oct-2-ene-6-carboxylic acid esters are produced by adding a Brønsted acid to a mixture of a 2-azabicyclo[2.2.1]hept-5-en-3-one and an alcohol, thereby causing these components to react with each other to give a salt of cis-4-amino-2-cyclopentene-1-carboxylic acid ester, then allowing the salt of cis-4-amino-2-cyclopentene-1-carboxylic acid ester thus obtained to react with an amino-protecting group introducing compound in the presence of a base, thereby giving cis-4-N-substituted amino-2-cyclopentene-1-carboxylic acid ester, and then allowing this cis-4-N-substituted amino-2-cyclopentene-1-carboxylic acid ester to react with a hypohalogenite and an aldoxime.

  4-N-取代氨基-2-氮杂-1-氧杂双环[3.3.0]辛-2-烯-6-羧酸酯是通过向2-氮杂双环[2.2.1]庚-5-烯-3-酮和醇的混合物中加入Brønsted酸，使这些组分相互反应以形成顺式-4-氨基-2-环戊烯-1-羧酸酯的盐，然后允许所得到的顺式-4-氨基-2-环戊烯-1-羧酸酯的盐在碱的存在下与氨基保护基引入化合物反应，从而给出顺式-4-N-取代氨基-2-环戊烯-1-羧酸酯，然后允许这种顺式-4-N-取代氨基-2-环戊烯-1-羧酸酯与次卤酸盐和醛肟反应而制得。
• METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE
  申请人：API CORPORATION

  公开号：US20140127762A1

  公开（公告）日：2014-05-08

  The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.

  本发明旨在提供一种工业方法，以在温和条件下通过少量步骤从非环状酮化合物中生产光学活性α-取代脯氨酸的方法。本发明涉及一种光学活性α-取代脯氨酸（4）和/或光学活性α-取代脯氨酰胺（5）的生产方法，包括以下步骤：(a)将非环状酮化合物（1）与氨、铵盐、一级胺和一级胺盐和氰化试剂中的至少一种反应，得到环状含氮化合物（2）；(b)使环状含氮化合物（2）水合，得到α-取代脯氨酰胺（3）；(c)通过(d)酶解水解、(e)对映异构盐形成的分离和/或(f)柱层析分离中的一种或多种方法来分离α-取代脯氨酰胺（3）。
• 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。