(S)-2-氨基-7-甲氧基四氢萘 | 121216-42-0

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (S)-2-氨基-7-甲氧基四氢萘
• 中文别名: (S)-2-(N-苄氨基)-7-甲氧基四氢萘；S-2-氨基-7-甲氧基四氢萘
• 英文名称: (S)-(1,2,3,4-tetrahydro-7-methoxy-2-naphthyl)amine
• 英文别名: (S)-2-amino-7-methoxytetralin；(2S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine；(S)-7-Methoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 121216-42-0
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: ZNWNWWLWFCCREO-JTQLQIEISA-N

物化性质

• 熔点：
  203 °C
• 沸点：
  299.6±40.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-氨基-7-甲氧基四氢萘 在 ammonium hydroxide 、 氢溴酸 作用下， 反应 3.0h， 以30%的产率得到(S)-2-氨基-7-羟基四氢化萘
  参考文献：
  名称：

  Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers

  摘要：

  A series of substituted phenylethanolaminotetralins were synthesized as pure stereoisomers and their ability to stimulate atypical beta-adrenoceptors selectively was evaluated. The compounds in vitro relative potencies were assessed using the atypical beta response of inhibition of rat proximal colon motility and the typical beta 1 (increase in guinea-pig right atrial frequency) and beta 2 (guinea-pig tracheal relaxation and rat uterus motility inhibition) responses. Compound 42 (SR 58611A) was found to be the most potent and selective.

  DOI：

  10.1016/0223-5234(94)90095-7
• 作为产物：
  描述：

  2-氨基-7-甲氧基四氢萘盐酸盐 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 异丙醇 、 甲苯 为溶剂， 反应 0.5h， 生成 (S)-2-氨基-7-甲氧基四氢萘
  参考文献：
  名称：

  Design and Optimization of Potent and Orally Bioavailable Tetrahydronaphthalene Raf Inhibitors

  摘要：

  Inhibition of mutant B-Raf signaling, through either direct inhibition of the enzyme or inhibition of MEK, the direct substrate of Raf, has been demonstrated preclinically to inhibit tumor growth. Very recently, treatment of B-Raf mutant melanoma patients with a selective B-Raf inhibitor has resulted in promising preliminary evidence of antitumor activity. This article describes the design and optimization of tetrahydronaphthalene-derived compounds as potent inhibitors of the Raf pathway in vitro and in vivo. These compounds possess good pharmacokinetic properties in rodents and inhibit B-Raf mutant tumor growth in mouse xenograft models.

  DOI：

  10.1021/jm101479y
• 作为试剂：
  描述：

  (S)-7-methoxy-2-azidotetralin 、 氢气 在 钯 氮 、 钯 、 甲苯 、 (S)-2-氨基-7-甲氧基四氢萘 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以was obtained (yield: 93%)的产率得到(S)-2-氨基-7-甲氧基四氢萘
  参考文献：
  名称：

  Process for preparation of 2-aminotetralin derivatives and intermediates thereof

  摘要：

  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。

  公开号：

  US20050153408A1

文献信息

• Malonamid and malonamic ester derivatives with antithrombotic activity, their preparation and their use
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1193248A1

  公开（公告）日：2002-04-03

  The present invention relates to compounds of the of the formula I, in which R1, R2, A and B have the meanings indicated in the claims. The compounds of the formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of thromboembolic diseases and restenoses. They are reversible inhibitors of the blood clotting enzyme factor VIIa and can in general be applied in conditions in which an undesired activity of factor VIIa is present or for the cure or prevention of which an inhibition of factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及式I化合物的化合物，其中R1，R2，A和B具有权利要求中指出的含义。式I的化合物是有价值的药理活性化合物。它们展现出强大的抗血栓作用，并适用于例如治疗和预防血栓栓塞性疾病和再狭窄。它们是血液凝固酶因子VIIa的可逆抑制剂，通常可以应用于因子VIIa存在不需要活性或治疗或预防因子VIIa抑制的情况。本发明还涉及用于制备式I化合物的方法，其用途，尤其是作为药品中的活性成分，以及包含它们的药物制剂。
• Asymmetric hydrogenation of trisubstituted N-acetyl enamides derived from 2-tetralones using ruthenium-SYNPHOS catalysts: a practical synthetic approach to the preparation of β3-adrenergic agonist SR58611A
  作者：Cyrielle Pautigny、Charlotte Debouit、Philippe Vayron、Tahar Ayad、Virgine Ratovelomanana-Vidal

  DOI：10.1016/j.tetasy.2010.03.024

  日期：2010.6

  asymmetric hydrogenation of various trisubstituted enamides derived from 2-tetralones under mild reaction conditions using Ru-SYNPHOS catalysts is reported. This practical and clean method gives access to several chiral 2-aminotetralins derivatives in high isolated yields and enantiomeric excesses up to 95% depending on the substitution pattern of the aromatic ring and the nature of the amide moiety.

  报道了使用Ru-SYNPHOS催化剂在温和的反应条件下衍生自2-四氢萘酮的各种三取代的烯酰胺的不对称氢化。这种实用，清洁的方法可以高分离度获得几种手性2-氨基四氢萘衍生物，对映体过量高达95％，具体取决于芳环的取代方式和酰胺部分的性质。此外，目前的方法的有效性是通过一个实际的合成方法，以对映异构纯SR58611A化合物，有效的和选择性β证明3 -肾上腺素能受体激动剂。
• Asymmetric Amination of Tetralone and Chromanone Derivatives Employing ω-Transaminases
  作者：Desiree Pressnitz、Christine S. Fuchs、Johann H. Sattler、Tanja Knaus、Peter Macheroux、Francesco G. Mutti、Wolfgang Kroutil

  DOI：10.1021/cs400002d

  日期：2013.4.5

  (S)-selective and (R)-selective ω-transaminases were investigated for the amination of 1- and 2-tetralone and derivatives as well as of 3- and 4-chromanone. All ketones tested were aminated to give the corresponding enantiopure amines (ee > 99%) employing at least one of the enzymes investigated. In most of the cases the (S)- as well as the (R)-enantiomer was obtained in optically pure form. The amination of

  研究了各种（S）-选择性和（R）-选择性ω-转氨酶，用于1-和2-四氢萘酮及其衍生物以及3-和4-苯并二氢吡喃酮的胺化。使用至少一种所研究的酶，将所有测试的酮胺化，得到相应的对映纯胺（ee > 99％）。在大多数情况下，以光学纯的形式获得（S）-和（R）-对映体。3-苯并二氢吡喃酮的胺化反应在100 mg的规模上进行，得到光学纯的（R）-3-氨基苯并二氢吡喃（ee > 99％），具有完全转化率和78％的分离产率。
• Alternative synthesis of the chiral atypical β-adrenergicphenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation
  作者：Marc Devocelle、André Mortreux、Francine Agbossou、Jean-Robert Dormoy

  DOI：10.1016/s0040-4039(99)00807-2

  日期：1999.6

  We have developed an alternative synthesis of the atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A. Two key intermediates have been synthesised involving enantioselective hydrogenation of an aminoketone and an enamide providing the corresponding amino alcohol and amide in >96 and >98 % ee respectively.

  我们已经开发出非典型的β-肾上腺素苯基乙醇氨基四氢呋喃激动剂SR58611A的另一种合成方法。已合成了两种关键中间体，涉及对氨基酮和烯酰胺的对映选择性氢化，分别提供了> 96％ee和> 98％ee的相应氨基醇和酰胺。
• Novel aminotransferase, gene encoding the same, and method of using them
  申请人：Ito Noriyuki

  公开号：US20100285544A1

  公开（公告）日：2010-11-11

  The invention relates to a novel aminotransferase, DNA encoding the enzyme, a recombinant vector into which the DNA has been introduced, and a transformant into which the vector has been introduced. Further, the invention also relates to a method for producing an optically active amino compound utilizing the enzyme or transformant. The aminotransferase of the invention has an ability of efficiently converting a ketone compound, particularly a cyclic ketone compound to an optically active amino compound. According to the invention, a method for efficiently producing an optically active amino compound, particularly an optically active cyclic amino compound is provided.

  本发明涉及一种新型氨基转移酶、编码该酶的DNA、已引入该DNA的重组载体以及已引入该载体的转化菌株。此外，本发明还涉及一种利用该酶或转化菌株生产光学活性氨基化合物的方法。本发明的氨基转移酶能够高效地将酮类化合物，尤其是环状酮类化合物转化为光学活性氨基化合物。根据本发明，提供了一种高效生产光学活性氨基化合物，尤其是光学活性环状氨基化合物的方法。