(R)-N-methyl-2,3-dihydro-1H-inden-1-amine | 10277-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-N-methyl-2,3-dihydro-1H-inden-1-amine
• 英文别名: N-methyl-1(R)-aminoindan；(1R)-2,3-dihydro-N-methyl-1H-inden-1-amine；(1R)-N-methyl-2,3-dihydro-1H-inden-1-amine
• CAS: 10277-78-8
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: AIXUYZODYPPNAV-SNVBAGLBSA-N

物化性质

• 沸点：
  235.3±19.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride 、 (R)-N-methyl-2,3-dihydro-1H-inden-1-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[(1R)-2,3-dihydro-1H-inden-1-yl]-N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxamide
  参考文献：
  名称：

  WO2008/91594

  摘要：

  公开号：
• 作为产物：
  描述：

  (R)-(-)-1-氨基茚满 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (R)-N-methyl-2,3-dihydro-1H-inden-1-amine
  参考文献：
  名称：

  1,5-Asymmetric Induction in Squarate Cascades. Conformational Control of Helicity by Chiral Amino Substituents during Conrotatory Octatetraene Cyclization Prior to β-Elimination

  摘要：

  Both the sigmatropic and electrocyclic rearrangement pathways that can arise when a pair of alkenyl anions are added to a squarate ester have high stereochemical demands. The distinction is nontrivial. When cis addition occurs initially, the stereoinduction that materializes at this point is fully transmitted into the product(s). The more commonly observed trans addition exhibits fleeting stereochemical consequences because of rapid equilibration of the octatetraenyl intermediates. In this instance, product distribution is governed by the relative rates of conrotatory cyclization at this advanced stage. Herein reported is a complete dissection of a squarate cascade when a stereogenic center attached to an amino substituent effects 1,5-asymmetric induction prior to B-elimination of the entire fragment. Deuterium labeling permits a direct measure of the contrasting kinetic imbalances associated with the two possible modes of alkenyl anion addition. Furthermore; quantitative analysis of the partitioning experienced by the two helical octatetraenes is readily accomplished. This work constitutes the first example where a complete dynamic profile for these complex processes has been possible. The fact that long-range asymmetric induction has been instrumental in solving the mechanistic puzzle is noteworthy.

  DOI：

  10.1021/jo9722921

文献信息

• [EN] IAP INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINE D'APOPTOSE
  申请人：TETRALOGIC PHARM CORP

  公开号：WO2010138496A1

  公开（公告）日：2010-12-02

  The present invention describes compounds, processes for their preparation, pharmaceutical compositions containing them, and their use in therapy.

  本发明描述了化合物、其制备方法、含有它们的药物组合物，以及它们在治疗中的应用。
• [EN] COMPOUNDS USEFUL IN HIV THERAPY<br/>[FR] COMPOSÉS UTILES DANS LA THÉRAPIE DU VIH
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2020110056A1

  公开（公告）日：2020-06-04

  The invention relates to compounds of Formula (I), (Ia), (Ib), (II) or (III), salts thereof, pharmaceutical compositions thereof, as well as therapeutic methods of treatment and prevention.

  这项发明涉及到式(I)、(Ia)、(Ib)、(II)或(III)的化合物，以及它们的盐、药物组合物，以及治疗和预防的治疗方法。
• Tackling <i>N</i> ‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
  作者：Clemens K. Blasius、Niklas F. Heinrich、Vladislav Vasilenko、Lutz H. Gade

  DOI：10.1002/anie.202006557

  日期：2020.9.7

  catalyzes the highly enantioselective hydroboration of N‐alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N‐alkyl imines provided the corresponding α‐chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals

  易于活化的烷基铁预催化剂可有效催化N-烷基亚胺的高度对映选择性氢硼化。使用手性双（恶唑啉基亚甲基）异二氢吲哚钳配体，各种无环N-烷基亚胺的不对称还原提供了相应的α-手性胺，收率极高，ee高达99％以上。药物芬迪林和Tecalcet的合成进一步证明了该贱金属催化体系的适用性。
• [EN] A NEW METHOD FOR THE SYNTHESIS OF RASAGILINE<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE RASAGILINE
  申请人：FARGEM FARMASOETIK ARASTIRMA GELISTIRME MERKEZI SANAYI VE TICARET A S

  公开号：WO2012096635A1

  公开（公告）日：2012-07-19

  We have developed a new method for the synthesis of Rasagiline (Formula 1) based on the alkylation of trifluoroacetyl protected aminoindan. This protection enabled us to carry out an alkylation of aminoindan with a high yield and purity under very mild conditions with a wide range of reaction conditions and reagent selection. Considering the ease, purity and high yields of introducing and removal of the trifluoroacetyl group, this approach is a highly practical and economical way for the synthesis of rasagiline or its pharmaceutically acceptable salts.

  我们已经开发了一种基于三氟乙酰保护氨基茚的烷基化方法，用于合成拉沙吉林（Formula 1）。这种保护使我们能够在非常温和的条件下，在广泛的反应条件和试剂选择范围内高产率和纯度地进行氨基茚的烷基化。考虑到引入和去除三氟乙酰基的便捷性、纯度和高产率，这种方法是合成拉沙吉林或其药用可接受盐的一种高度实用和经济的途径。
• [EN] A PROCESS FOR THE PREPARATION OF (R)-I -AMINOINDANES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (R)-1-AMINOINDANES
  申请人：CHEMO IBERICA SA

  公开号：WO2010049379A1

  公开（公告）日：2010-05-06

  The present invention relates to a process for the preparation of the chiral compound of formula (V), wherein R1 is a C1-C6 alkyl group optionally substituted with halogens, an aryl optionally substituted, or a trialkyl silyl group, for use as an intermediate in the preparation of (R)-1-aminoindanes, helpful in the pharmaceutical field. The compound of formula (V) is a key intermediate to the preparation of (R)-1- aminoindanes, particularly Rasagiline. The invention also relates to novel compounds, which are especially useful as intermediates for the preparation of (R)-1- aminoindanes.

  本发明涉及一种制备手性化合物的方法，该化合物的化学式为（V），其中R1是一个C1-C6烷基，可以选择性地与卤素取代，也可以是一个芳基，或者是一个三烷基硅基团，用作(R)-1-氨基茚烷的制备中间体，在制药领域中有帮助。化合物的化学式（V）是(R)-1-氨基茚烷的制备的关键中间体，特别是Rasagiline。该发明还涉及新化合物，特别适用作(R)-1-氨基茚烷的制备中间体。