1-(1-naphthalenyl)-prop-2-en-1-amine | 1186139-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-naphthalenyl)-prop-2-en-1-amine
• 英文别名: 1-(naphthalen-1-yl)prop-2-en-1-amine；1-(naphth-1-yl)-allylamine；1-(Napht-1-yl)-allylamine；1-naphthalen-1-ylprop-2-en-1-amine
• CAS: 1186139-06-9
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: HHROCIPRSSACTK-UHFFFAOYSA-N

物化性质

• 沸点：
  333.1±11.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-naphthalenyl)-prop-2-en-1-amine 在 [(DPEphos)Rh(COD)]BF₄ 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Regio- and Chemoselective Intermolecular Hydroamination of Allyl Imines for the Synthesis of 1,2-Diamines

  摘要：

  The synthesis of 1,2-diamines via a Rh-catalyzed intermolecular hydroamination of N-allyl imines with cyclic amines is presented. Coordinating groups proximal to the olefin bind to the catalyst and promote the transformation. The reaction affords 1,2-diamines in very good yields and is functional-group-tolerant and highly diastereoselective.

  DOI：

  10.1021/ja505794u
• 作为产物：
  描述：

  (E)-3-(1-naphthyl)prop-2-en-1-ol 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 48.25h， 生成 1-(1-naphthalenyl)-prop-2-en-1-amine
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004

文献信息

• [EN] NEW CHIRAL STATIONARY PHASES FOR CHROMATOGRAPHY BASED ON AROMATIC ALLYL AMINES<br/>[FR] NOUVELLES PHASES STATIONNAIRES CHIRALES POUR CHROMATOGRAPHIE À BASE D'AMINES D'ALLYLE AROMATIQUES
  申请人：RUDJER BOSKOVIC INST

  公开号：WO2009109792A1

  公开（公告）日：2009-09-11

  New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.

  基于手性选择剂共价结合在固体支持上的新手性固定相（CSPs）已经制备。手性选择剂是从对映异构纯芳香胺和3,5-二硝基苯甲酸中获得的，然后通过烯丙基双键连接到支持表面。这样获得的材料可以用于拆分混合物或对映富集化合物的手性分离。这些手性固定相可以作为色谱柱中的填料，通过高效液相色谱在分析和制备尺度上对萘普生类药物和其他类似的非甾体类抗炎药物（NSAID）进行对映异构体分离。
• Catalyst for asymmetric (transfer) hydrogenation
  申请人：——

  公开号：US20030199713A1

  公开（公告）日：2003-10-23

  Catalyst for the asymmetric (transfer) hydrogenation represented by the formula ML a X b S c , where M is a transition metal, to be chosen from rhodium and ruthenium, and X is a counter ion and S is a ligand, a ranges from 0.5 to 3 and b and c, each independently, range from 0 to 2, and L is a chiral ligand having the formula (1), where C n together with the two 2 O-atoms and the P-atom forms a substituted or non-substituted ring with 2-4 C-atoms, R 1 and R 2 each independently represent H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group or may form a (heterocyclic) ring together with the N-atom to which they are bound. And a process for the asymmetric (transfer) hydrogenation of an olefinically unsaturated compound, ketone, imine or oxime derivate in the presence of a hydrogen donor and of a catalyst, use being made of a catalyst represented by formula ML a X b S c , where M is a transition metal, to be chosen from rhodium, iridium and ruthenium, X is a counter ion, S is a ligand, a ranges from 0.5 to 3 and b and c range from 0 to 2, and L is a chiral ligand having the formula (1), where C n together with the two 2 O-atoms and the P-atom forms a substituted or non-substituted ring with 2-4 C-atoms; and R 1 and R 2 are as defined above.

  催化剂用于不对称（转移）氢化反应，其表示为M为过渡金属，可选自铑和钌，X为反离子，S为配体，a范围为0.5至3，b和c各自独立地范围为0至2，L为手性配体，其化学式为（1），其中Cntogether与两个氧原子和磷原子形成具有2-4个碳原子的取代或非取代环，R1和R2各自独立地代表氢，或可选地取代的烷基，芳基，烷芳基或芳烷基，或者与它们结合的氮原子一起形成（杂环）环。一种用于不对称（转移）氢化烯烃不饱和化合物，酮，亚胺或肟衍生物的方法，在氢供体和催化剂存在下进行，所用催化剂的化学式为MLaXbSc，其中M为过渡金属，可选自铑，铱和钌，X为反离子，S为配体，a范围为0.5至3，b和c范围为0至2，L为手性配体，其化学式为（1），其中Cntogether与两个氧原子和磷原子形成具有2-4个碳原子的取代或非取代环；R1和R2如上所定义。
• [EN] BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, AND BENZODIOXANE MELATONERGIC AGENTS<br/>[FR] LES BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, ET BENZODIOXANE: DES AGENTS MELATONERGIQUES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1998025606A1

  公开（公告）日：1998-06-18

  (EN) Novel derivatives of benzodioxole, benzofuran, 2,3-dihydrobenzofuran, and benzodioxane are useful as melatonergic agents.(FR) La présente invention concerne de nouveaux dérivés des benzodioxole, benzofuran, 2,3-dihydrobenzofuran, et benzodioxane qui conviennent particulièrement comme agents mélatonergiques.

  这段话的中文翻译如下： (EN) Novel derivatives of benzodioxole, benzofuran, 2,3-dihydrobenzofuran, and benzodioxane are useful as melatonergic agents. (中) 新型苯并二氧杂环、苯并呋喃、2,3-二氢苯并呋喃和苯并二氧杂环的衍生物可作为褪黑素能药物使用。 (FR) La présente invention concerne de nouveaux dérivés des benzodioxole, benzofuran, 2,3-dihydrobenzofuran, et benzodioxane qui conviennent particulièrement comme agents mélatonergiques. (中) 本发明涉及苯并二氧杂环、苯并呋喃、2,3-二氢苯并呋喃和苯并二氧杂环的新型衍生物，特别适用于作为褪黑素能药物。
• Chiral Compound Suitable as a Catalyst for Asymmetric Transfer Hydrogenation
  申请人：Vries De Johannes Gerardus (Hans)

  公开号：US20080269529A1

  公开（公告）日：2008-10-30

  The invention relates to an enantiomerically enriched chiral compound comprising a transition metal M, which comprises four, five or six coordinating groups of which at least one pair is linked together to form a bidentate ligand, in which M is directly bound via one single σ-bond to a carbon atom of an optionally substituted and/or optionally fused (hetero)aromatic ring of said bidentate ligand and in which M is directly bound to a nitrogen atom of a primary or secondary amino group of said bidentate ligand, thereby forming a metallacycle between said bidentate ligand and the metal M, said metal M being selected from the metals of groups 8 and 9 of the Periodic Table of the Elements, in particular iron, ruthenium, osmium, cobalt, rhodium, or iridium. The chiral compound can be used as a catalyst, preferably in an asymmetric transfer hydrogenation process. The invention further relates to a process for an asymmetric transfer hydrogenation of a prochiral compound in the presence of a hydrogen donor and the chiral compound of the invention comprising a transition metal chosen from the metals of groups 8, 9 and 10 of the Periodic Table, in particular iron, ruthenium, osmium, cobalt, rhodium, iridium, nickel, palladium or platinum as the catalyst.

  本发明涉及一种手性化合物，其中包含过渡金属M，该金属包含四个、五个或六个配位基团，其中至少一对基团连接在一起形成双齿配体。在该双齿配体的一个可选取代和/或可选融合的(杂)芳香环的碳原子上，M通过一个单一的σ键直接结合，并且M直接与双齿配体的一级或二级氨基团的氮原子结合，从而在双齿配体和金属M之间形成一个金属环。所述金属M选自元素周期表第8和第9组的金属，特别是铁、钌、锇、钴、铑或铱。该手性化合物可用作催化剂，优选在不对称转移氢化过程中使用。本发明还涉及一种在氢供体和来自元素周期表第8、9和10组的金属中选择的过渡金属，特别是铁、钌、锇、钴、铑、铱、镍、钯或铂作为催化剂的不对称转移氢化的过程。
• Chiral Stationary Phases For Chromatography Based On Aromatic Allyl Amines
  申请人：Vinkovic Vladimir

  公开号：US20110094966A1

  公开（公告）日：2011-04-28

  New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.

  制备了基于手性选择剂共价结合于固体支持上的新手性固定相（CSPs）。手性选择剂是由对映异构体纯的芳香胺和3,5-二硝基苯甲酸制备的，然后通过烯丙基双键连接到支持表面上。这种材料可以对混合物或手性富集化合物进行对映异构体分离。这些手性固定相可以作为色谱柱填充物，在高效液相色谱分析和制备级别上用于萘普生类药物和其他类似非甾体抗炎药（NSAID）的对映体分离。