(S)-4-硝基-Alpha-甲基苄胺 | 4187-53-5

• 物质功能分类: 有机原料 - 氨基化合物
• 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: (S)-4-硝基-Alpha-甲基苄胺
• 中文别名: (S)-4-硝基-Α-甲基苄基胺；(S)-4-硝基-α-甲基苄胺
• 英文名称: (S)-1-(p-nitrophenyl)ethylamine
• 英文别名: (S)-1-(4-nitrophenyl)ethylamine；(S)-1-(4-nitrophenyl)ethan-1-amine；(S)-1-(4-nitrophenyl)ethanamine；(1S)-1-(4-nitrophenyl)ethanamine
• CAS: 4187-53-5
• 化学式: C₈H₁₀N₂O₂
• mdl: MFCD00137390
• 分子量: 166.18
• InChiKey: RAEVOBPXEHVUFY-LURJTMIESA-N

物化性质

• 沸点：
  120-121 °C(Press: 1 Torr)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-硝基-Alpha-甲基苄胺 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists

  摘要：

  A series of alpha-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of alpha-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.054
• 作为产物：
  描述：

  (E)-N-[1-(4-硝基苯基)亚乙基]羟胺 在 硼烷四氢呋喃络合物 、 (S)-proline (R)-1,1'-bi(2-naphthyl)dioxyboryl ester 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (S)-4-硝基-Alpha-甲基苄胺
  参考文献：
  名称：

  Asymmetric Reduction of Oxime Ethers Promoted by Chiral Spiroborate Esters with an O₃BN Framework

  摘要：

  Enatioselective reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework is reported for the first time. In the presence of (R,S)-1, 11 aralkyloxime ethers are reduced by borane-THF at 0-5 degrees C to give (S)-1-aralkylamine in high yield and excellent enatiomeric excess (up to 98% ee). Influence of reaction conditions on the enantioselectivity of the reduction is investigated, and a possible mechanism of the catalytic reduction is suggested.

  DOI：

  10.1021/jo060123n
• 作为试剂：
  描述：

  1,4-苯并二烷-2-羧酸 在 (S)-4-硝基-Alpha-甲基苄胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以2.33 g的产率得到(S)-2,3-二氢-1,4-苯并二噁英-2-羧酸
  参考文献：
  名称：

  Highly efficient resolutions of 1,4-benzodioxane-2-carboxylic acid with para substituted 1-phenylethylamines

  摘要：

  The salts of (S)- and (R)-1.4-benzodioxane-2-carboxylic acid with eight (S)-1-arylethylamines were prepared. The determination of their melting points and of their solubilities in alcohol solvents revealed large differences between the diastereomeric benzodioxanecarboxylates of (S)-1-(p-nitrophenyl)ethylamine and of (S)-1-(p-methylphenyl)ethylamine. Therefore, these latter amines were selected to resolve (+/-)-1,4-benzodioxane-2-carboxylic acid by diastereoselective crystallization finding that both of them display a very high resolution ability for such a substrate, which contrasts with the null efficiency of unsubstituted 1-phenylethylamine. These results are consistent with DSC evidences, which indicated that the two successfully resolved diastereomeric systems are binary mixtures exhibiting a eutectic with a high content of the more soluble diastereomeric salt. The new procedures can advantageously replace the two resolutions we had previously reported, that of the same acid with dehydroabietylamine and that of glycerol acetonide, a precursor of 1,4-benzodioxane-2-carboxylic acid, with I-phenylethylamine. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.052

文献信息

• Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (<i>E</i>)- and (<i>Z</i>)-<i>O</i>-Benzyloximes: Applications toward the Synthesis of Calcimimetic Agents
  作者：Wenhua Ou、Sandraliz Espinosa、Héctor J. Meléndez、Silvia M. Farré、Jaime L. Alvarez、Valerie Torres、Ileanne Martínez、Kiara M. Santiago、Margarita Ortiz-Marciales

  DOI：10.1021/jo400371x

  日期：2013.6.7

  Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst

  使用衍生自稳定的螺硼酸酯，通过硼烷介导的单一异构体 ( E )- 和 ( Z ) -O-苄基肟醚的还原，合成了高对映体纯的 (1-芳基)-和 (1-萘基)-1-乙胺( S )-二苯基缬氨醇和乙二醇作为手性催化剂。伯 ( R )-芳基乙胺是通过使用 15% 的催化剂将纯 ( Z )-乙酮肟醚还原至 99% ee来制备的。描述了使用对映纯(1-萘-1-基)乙胺作为手性前体合成新的和已知的拟钙剂类似物的两种方便且容易的方法。
• Process for the synthesis of intermediates useful for the synthesis of tubulin inhibitors
  申请人：Wyeth Holdings Corporation

  公开号：US20040063904A1

  公开（公告）日：2004-04-01

  The invention is a process for the preparation of compounds of the Formula I: 1 where R 1 , R 2 , R 3 , R 4 and R 5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors which are useful in the treatment of cancer.

  这项发明是一种用于制备式I化合物的方法： 1 其中R 1 ，R 2 ，R 3 ，R 4 和R 5 在规范中有定义，这些中间体对于制备对抗癌症治疗中有用的微管蛋白抑制剂是有用的。
• [EN] THIENOPYRIDINE DERIVATIVES, PRODUCTION METHOD AND USE THEREOF<br/>[FR] DÉRIVÉS DE THIÉNOPYRIDINE, MÉTHODE DE PRODUCTION ET LEUR UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2005111046A1

  公开（公告）日：2005-11-24

  A compound represented by the formula (I) wherein R is a hydrogen atom or a C1-4 alkyl group, and X is CH2, O or S, or a salt thereof. The present invention provides a novel thienopyridine derivative having an anti-inflammatory effect, a bone resorption suppressing effect, an immune cytokine production suppressing effect and the like, and useful as a pharmaceutical agent such as an agent for the prophylaxis or treatment of arthritis such as rheumatoid arthritis and the like, and the like, and the like.

  本发明提供了一种含有公式(I)所表示的化合物，其中R是氢原子或C1-4烷基团，X是CH2、O或S，或其盐。该发明提供了一种具有抗炎作用、抑制骨吸收作用、抑制免疫细胞因子产生作用等新颖的噻吩并吡啶衍生物，并可作为预防或治疗类风湿性关节炎等关节炎的药物等。
• 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。
• Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase
  作者：Garrett Hellinghausen、Diego A. Lopez、Jauh T. Lee、Yadi Wang、Choyce A. Weatherly、Abiud E. Portillo、Alain Berthod、Daniel W. Armstrong

  DOI：10.1002/chir.22985

  日期：2018.9

  macrocyclic glycopeptide‐based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide‐based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide‐based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary

  通过对万古霉素的Edman降解制备的修饰的基于大环糖肽的手性固定相（CSP）被首次评估为手性选择剂。将其适用性与其他基于大环糖肽的CSP（TeicoShell和VancoShell）进行了比较。此外，还进一步检查了另一种基于大环糖肽的修饰CSP NicoShell。最初的评估集中在与这些糖肽的互补行为上。根据以前的工作，使用了一种筛选方法，用于对50种手性化合物的对映体分离，其中包括氨基酸，农药，兴奋剂和多种药物。使用表面多孔（核-壳）颗粒载体可实现快速有效的手性分离。总体，万古霉素埃德曼降解产物（EDP）与TeicoShell类似，在极性离子模式下对酸性化合物具有高对映选择性。使用液相色谱-质谱联用EDP同时分离5种外消旋脯氨酸的对映异构体，时间约为3分钟。其他亮点包括同时用VancoShell液相色谱分离rac-amphetamine和rac-methamphetamine，用Nico