(2S)-6-溴-1,2,3,4-四氢萘-2-醇 | 171965-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (2S)-6-溴-1,2,3,4-四氢萘-2-醇
• 英文名称: (S)-6-bromo-β-tetralol
• 英文别名: (2S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-ol
• CAS: 171965-24-5
• 化学式: C₁₀H₁₁BrO
• 分子量: 227.101
• InChiKey: GFAONWSTEKWMAV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 (2S)-6-溴-1,2,3,4-四氢萘-2-醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以90%的产率得到Methanesulfonic acid (S)-6-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Asymmetric Synthesis of MK-0499

  摘要：

  Described herein is an efficient asymmetric synthesis of the potent antiarrhthymia agent MK-0499. The route is convergent and is highlighted by two stereoselective reactions. A ruthenium-catalyzed, enantioselective hydrogenation of an enamide was developed for the preparation of the key amine intermediate. Oxazaborolidine-mediated ketone reduction was utilized to establish the alcohol stereochemistry. Optimization of this chemistry led to an IPA modified reduction method which provides enhanced stereoselectivity.

  DOI：

  10.1021/jo00119a008
• 作为产物：
  描述：

  6-溴-2-四氢萘酮 反应 24.0h， 生成 (2S)-6-溴-1,2,3,4-四氢萘-2-醇
  参考文献：
  名称：

  Asymmetric Synthesis of MK-0499

  摘要：

  Described herein is an efficient asymmetric synthesis of the potent antiarrhthymia agent MK-0499. The route is convergent and is highlighted by two stereoselective reactions. A ruthenium-catalyzed, enantioselective hydrogenation of an enamide was developed for the preparation of the key amine intermediate. Oxazaborolidine-mediated ketone reduction was utilized to establish the alcohol stereochemistry. Optimization of this chemistry led to an IPA modified reduction method which provides enhanced stereoselectivity.

  DOI：

  10.1021/jo00119a008

文献信息

• [EN] SUBSTITUTED BICYCLIC COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES SUBSTITUÉS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016028959A1

  公开（公告）日：2016-02-25

  Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V) and/or a salt thereof, wherein R1 is OH or OP(O)(OH)2, and X1, X2, X3, R2, R2a, Ra, Rb, and Rc are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula（I）、（II）、（III）、（IV）和（V）及/或其盐的化合物，其中R1为OH或OP（O）（OH）2，X1、X2、X3、R2、R2a、Ra、Rb和Rc在此处有定义。还揭示了将这些化合物用作选择性G蛋白偶联受体S1P1的激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或疾病的进展方面是有用的，如自身免疫疾病和血管疾病。
• Process for preparation of 2-aminotetralin derivatives and intermediates thereof
  申请人：Honda Tatsuya

  公开号：US20050153408A1

  公开（公告）日：2005-07-14

  The present invention is to efficiently and simply prepare an optically active 7-substituted-2-aminotetralin with industrial advantage. In the process, a 7-substituted-2-tetralone or its bisulfite adduct is reduced with a microorganism to an optically active 7-substituted-2-tetralol. Then, a sulfonyl group is introduced to the hydroxy group to form an optically active 7-substituted-2-sulfonyloxytetralin. Then, with inversion of the configuration, a nitrogen substituent is introduced using a nitrogen nucleophile to form an optically active 2,7-substituted tetralin. Furthermore, if necessary, the nitrogen substituent is converted into a non-substituted amino group. Thus, an optically active 7-substituted-2-aminotetralin or its salt is prepared.

  本发明旨在以工业优势高效简便地制备光学活性的7-取代-2-氨基四氢萘。在该过程中，使用微生物将7-取代-2-四氢萘酮或其亚硫酸盐加合物还原为光学活性的7-取代-2-四氢萘醇。然后，引入磺酰基到羟基上，以形成光学活性的7-取代-2-磺酰氧基四氢萘。接着，通过构型反演，使用氮亲核试剂引入氮取代基，以形成光学活性的2,7-取代四氢萘。此外，如有必要，氮取代基可转化为非取代的氨基。因此，制备了光学活性的7-取代-2-氨基四氢萘或其盐。
• PROCESS FOR PREPARATION OF 2-AMINOTETRALIN DERIVATIVES AND INTERMEDIATES THEREOF
  申请人：KANEKA CORPORATION

  公开号：EP1457570A1

  公开（公告）日：2004-09-15

  The present invention is to efficiently and simply prepare an optically active 7-substituted-2-aminotetralin with industrial advantage. In the process, a 7-substituted-2-tetralone or its bisulfite adduct is reduced with a microorganism to an optically active 7-substituted-2-tetralol. Then, a sulfonyl group is introduced to the hydroxy group to form an optically active 7-substituted-2-sulfonyloxytetralin. Then, with inversion of the configuration, a nitrogen substituent is introduced using a nitrogen nucleophile to form an optically active 2,7-substituted tetralin. Furthermore, if necessary, the nitrogen substituent is converted into a non-substituted amino group. Thus, an optically active 7-substituted-2-aminotetralin or its salt is prepared.

  本发明旨在高效、简单地制备具有工业优势的光学活性 7-取代-2-氨基四氢萘。 在制备过程中，用微生物将 7-取代-2-四氢萘酮或其亚硫酸氢盐加合物还原成具有光学活性的 7-取代-2-四氢萘酚。然后，在羟基上引入磺酰基，形成具有光学活性的 7-取代-2-磺酰氧基四氢萘。然后，在反转构型的情况下，使用氮亲核剂引入一个氮取代基，形成具有光学活性的 2,7-取代四氢萘。此外，如有必要，还可将氮取代基转化为非取代氨基。这样，一种具有光学活性的 7-取代-2-氨基四氢萘或其盐就制备出来了。
• Asymmetric Synthesis of MK-0499
  作者：David M. Tschaen、Lee Abramson、Dongwei Cai、Richard Desmond、Ulf-H. Dolling、Lisa Frey、Sandor Karady、Yao-Jun Shi、Thomas R. Verhoeven

  DOI：10.1021/jo00119a008

  日期：1995.7

  Described herein is an efficient asymmetric synthesis of the potent antiarrhthymia agent MK-0499. The route is convergent and is highlighted by two stereoselective reactions. A ruthenium-catalyzed, enantioselective hydrogenation of an enamide was developed for the preparation of the key amine intermediate. Oxazaborolidine-mediated ketone reduction was utilized to establish the alcohol stereochemistry. Optimization of this chemistry led to an IPA modified reduction method which provides enhanced stereoselectivity.
• An alternative bioreactor concept for application of an isolated oxidoreductase for asymmetric ketone reduction
  作者：Vicky J. Shorrock、Michel Chartrain、John M. Woodley

  DOI：10.1016/j.tet.2003.11.060

  日期：2004.1

  In this paper an isolated NADH dependent ketone reductase has been used to synthesise (S)-6-bromo-beta-tetralol from 6-bromo-beta-tetralone, together with commercially available formate dehydrogenase (FDH) as a recycle enzyme to produce preparative quantities of the product. Furthermore, initial experiments indicate potential for an alternative bioreactor concept via the use of a resin (XAD L-323) to bind the product (and residual substrate) of the conversion rather than the cofactors or enzymes, thus allowing a new method of recycle, potentially overcoming existing problems. (C) 2003 Published by Elsevier Ltd.